Home Halogen bonding in crystal structure of bis(1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium triiodide, C16H32CsI3O8
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Halogen bonding in crystal structure of bis(1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium triiodide, C16H32CsI3O8

  • Samir Haj Bloukh and Zehra Edis 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

C16H32CsI3O8, triclinic, P1̄ (no. 2), a = 10.7930(5) Å, b = 11.5610(5) Å, c = 12.4880(5) Å, α = 73.050(10)°, β = 88.870(10)°, γ = 66.060(10)°, V = 1353.62(16) Å3, Z = 2, Rgt(F) = 0.0578, wRref(F2) = 0.1875, T = 293(2) K.

CCDC no.: 1977339

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:Reddish-brown polyhedron
Size:0.30 × 0.25 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:4.8 mm−1
Diffractometer, scan mode:KappaCCD, ω
θmax, completeness:26.5°, 90%
N(hkl)measured, N(hkl)unique, Rint:4853, 4853,
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4166
N(param)refined:258
Programs:Diamond [1], CAD-4 [2], SHELX [3], [4]
Table 2:

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

AtomxyzUiso*/Ueq
Cs0.36854(8)0.42183(7)−0.21734(8)0.0538(3)
I10.5000000.0000000.5000000.0446(3)
I20.23561(9)0.11040(10)0.36787(8)0.0626(3)
I30.0000000.0000000.0000000.0441(3)
I4−0.21930(11)0.19988(12)−0.17295(10)0.0860(4)
O10.1124(8)0.4182(8)−0.1014(7)0.0480(19)
O20.3444(8)0.1692(8)−0.0486(7)0.0474(19)
O30.3301(8)0.1992(8)−0.2842(7)0.050(2)
O40.0954(9)0.4446(8)−0.3370(7)0.054(2)
O50.3400(10)0.6302(9)−0.4481(9)0.063(2)
O60.1620(10)0.7223(9)−0.2905(8)0.062(2)
O70.3787(11)0.6442(11)−0.1242(8)0.067(3)
O80.5586(11)0.5675(10)−0.2827(9)0.069(3)
C10.1054(13)0.2993(12)−0.0333(11)0.052(3)
H1A0.0749010.259715−0.0798150.062*
H1B0.0410170.3188700.0212130.062*
C20.2463(14)0.2037(13)0.0270(9)0.052(3)
H2A0.2750280.2441740.0738050.062*
H2B0.2419630.1234260.0760130.062*
C30.3434(13)0.0667(11)−0.0891(11)0.052(3)
H3A0.2506380.076411−0.1005180.062*
H3B0.395983−0.019724−0.0346730.062*
C40.4050(13)0.0770(13)−0.1989(12)0.058(3)
H4A0.4974680.067638−0.1861080.070*
H4B0.4098310.004227−0.2249640.070*
C50.2051(14)0.2103(15)−0.3291(12)0.060(3)
H5A0.1535900.185955−0.2688900.072*
H5B0.2215670.151826−0.3750100.072*
C60.1271(15)0.3542(16)−0.4002(12)0.065(4)
H6A0.1810190.376693−0.4590300.078*
H6B0.0430110.364145−0.4361580.078*
C7−0.0169(12)0.4564(14)−0.2771(11)0.057(3)
H7A−0.0212050.370668−0.2493840.068*
H7B−0.0999160.518725−0.3263780.068*
C8−0.0058(13)0.5038(14)−0.1811(12)0.060(3)
H8A−0.0050370.590928−0.2103380.072*
H8B−0.0863630.514050−0.1420230.072*
C90.2027(15)0.7218(16)−0.4755(11)0.066(4)
H9A0.1466840.673581−0.4732310.079*
H9B0.1906300.779823−0.5520910.079*
C100.1542(15)0.8040(15)−0.4006(14)0.072(4)
H10A0.2097400.852401−0.4014700.086*
H10B0.0606020.868192−0.4265280.086*
C110.1510(17)0.7807(19)−0.2026(17)0.081(5)
H11A0.1221010.731085−0.1381360.097*
H11B0.0804140.870939−0.2281180.097*
C120.274(2)0.7846(19)−0.167(2)0.099(6)
H12A0.2592770.826174−0.1077560.118*
H12B0.3044440.835456−0.2295500.118*
C130.5069(18)0.6462(16)−0.1243(12)0.071(4)
H13A0.5709390.563908−0.0709460.085*
H13B0.5021890.718707−0.0978170.085*
C140.5616(16)0.6618(17)−0.2357(14)0.070(4)
H14A0.5074310.750441−0.2862550.084*
H14B0.6547020.651959−0.2263030.084*
C150.5652(16)0.6016(17)−0.4012(14)0.071(4)
H15A0.6052750.519782−0.4207830.085*
H15B0.6269410.644803−0.4186900.085*
C160.4349(15)0.6893(16)−0.4744(12)0.067(4)
H16A0.3978610.775826−0.4627350.081*
H16B0.4506440.701547−0.5528870.081*

Source of material

Iodine (>=99.0%), caesium iodide, 1,4,7,10-tetraoxacyclododecan (12-crown-4) and ethanol were received from Sigma-Aldrich Chemical Co. (St. Louis, MO, USA). All the used reagents were of analytical grade and were used as purchased without further purification. The Raman spectra were measured using a Jobin Yvon U 100 spectrometer from Spectra-Physics (Argon laser at 514.5 nm). The title compound was synthesized by dissolving 0.16 g (0.63 mmol) of CsI and 0.16 g (0.63 mmol) I2 in 10 mL ethanol/10 ml methanol mixture at room temperature. Then 0.2 mL (1.26 mmol) 12-crown-4 is added under continuous stirring. The clear solution gives after 4 days at room temperature reddish-brown crystals of [Cs(12-crown-4)2]I3.

Experimental details

A reddish-brown single crystal was selected from the mother liquor and transferred to the Kappa CCD diffractometer [2]. The measurement was done at 293 K. The structure solution, refinement and further calculations were done with the programs SHELXL [3], [4]. The data collection was undertaken several years ago using a point detector. Unfortunately, the measured section produced a completeness of only ∼90%. Nevertheless during the refinement no correlation effects were detected.

Comment

Polyiodides are interesting compounds with a rich chemistry and many applications, especially as antimicrobial agents [5]. Previously, polyiodides and iodine were incorporated into cellulose membranes [6], polymer foams [7], silicon membranes [8] and wound dressing applications in form of nanoparticles [9] due to their microbicidal actions. Only few examples of polyiodides with 12-crown-4 and alkalimetal cations have been reported previously [10], [11]. In these compounds, the crown ether and the metal cation stabilize the polyiodide structures by forming sandwich structures [10], [11]. The long time stability of a polyiodide is important for its use as antimicrobial agent to increase its long term effectiveness, durability and reduce the iodine sublimation [6]. Triiodides seem to be the most interesting class of polyiodides due to their stability. There are hundreds of examples of triiodides in the literature [12]. Halogen bonding is a major factor of stability in polyiodides within three-center-systems [13] and their resulting antimicrobial activity [14].

The asymmetric unit of the title structure contains two crystallographically independent, isolated, symmetrical, linear triiodide anions I3− with crystallographic inversion symmetry. The bond lengths and angles within these structures are in expected ranges and are another example of a three-center-system [I-I-I]− with halogen bonding like the previously reported triiodies in our group [14]. This three-center-system is an indicator for possible antimicrobial activities. As reported before [14], the complex compound interacts with the cell membrane of the microorganism due to electrostatic interactions and is deformed. This results in gradual free molecular iodine release from the triiodide-unit. Iodine directly attacks the pathogens by destroying their cell membrane and causing protein oxidation [5], [9], [14]. There is only one strong Raman stretching vibration at 108 cm−1 for the triiodide, which is available in our previous compounds [14] and in the very recently reported cyclic I10−2 anion [15]. The later showed another strong line at 172 cm−1 due to weak connections to two neighboring halogen bond donors. Usually, covalent I2 is detected at around 180 cm−1 [13], [15]. All geometric parameters of the cationic cesium bis(12-crown-4) complex are in the expected ranges [16].

Acknowledgements

We are thankful to University of Cologne, Germany and Ajman University, Ajman, UAE for providing us with the funds. Funding for this research was provided by: Universität zu Köln (Graduiertenkolleg of the University of Cologne “Classification of phase transitions in crystalline compounds on account of structural and physical anomalies” to Z. Edis); Ajman University-IRG Research Grant (2018-A-PH-01). We are very grateful to Guido J. Reiss for his help managing the structural data.

References

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Received: 2019-12-15
Accepted: 2020-01-14
Published Online: 2020-02-12
Published in Print: 2020-04-28

©2020 Samir Haj Bloukh 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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  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
https://doi.org/10.1515/ncrs-2019-0915
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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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