Home 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
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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

  • Guido J. Reiss EMAIL logo and Alena Sergeeva
Published/Copyright: May 5, 2020
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 4

Abstract

C10H16I4ZnN2, monoclinic, P21 (no. 4), a = 7.3340(1) Å, b = 14.4781(3) Å, c = 8.6768(2) Å, β = 94.919(2)°, V = 917.93(3) Å3, Z = 2, Rgt(F) = 0.0165, wRref(F2) = 0.0397, T = 110 K.

CCDC no.: 1998655

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:0.47 × 0.25 × 0.19 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:8.05 mm−1
Diffractometer, scan mode:Xcalibur, ω
θmax, completeness:34.7°, >99%
N(hkl)measured, N(hkl)unique, Rint:57483, 7606, 0.036
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 7483
N(param)refined:159
Programs:CrysAlisPRO [1], SHELX [2], [3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
Zn10.21305(5)0.56284(3)0.72719(4)0.01823(7)
I10.56551(3)0.56807(2)0.69202(2)0.01969(4)
I20.13553(3)0.40892(2)0.86430(2)0.02181(5)
I30.05004(3)0.58628(2)0.45047(2)0.01973(4)
I40.12780(3)0.69623(2)0.91159(3)0.02215(5)
N10.7996(4)0.5366(2)0.0764(3)0.0219(6)
H10.8945780.5356750.0247780.12(4)*
C20.7447(5)0.4568(3)0.1376(4)0.0210(6)
H20.8096250.4025540.1245540.025*
C30.5912(4)0.4557(2)0.2200(4)0.0185(5)
C40.4974(5)0.5383(2)0.2363(4)0.0209(6)
H40.3935340.5392160.2906860.025*
C50.5580(5)0.6193(3)0.1719(4)0.0229(6)
H50.4949670.6744350.1821050.028*
C60.7144(5)0.6169(3)0.0917(4)0.0226(6)
H60.7587270.6705980.0494580.027*
N1’0.5881(4)0.3699(2)0.4672(3)0.0199(5)
H1’0.5647(13)0.427(3)0.5016(19)0.017(11)*
C2’0.5342(5)0.3676(2)0.2940(4)0.0193(6)
H2’0.5977960.3159850.2489460.023*
C3’0.3264(5)0.3460(3)0.2823(4)0.0261(7)
H3A0.2565780.3994920.2444920.031*
H3B0.2985120.2949300.2117940.031*
C4’0.2788(5)0.3207(3)0.4453(5)0.0267(7)
H4A0.2132270.3707340.4902620.032*
H4B0.2036970.2655000.4431180.032*
C5’0.4615(5)0.3041(3)0.5369(4)0.0236(6)
H5A0.4540900.3171520.6458050.028*
H5B0.5015450.2407410.5256360.028*
C6’0.7847(5)0.3500(3)0.5088(6)0.0327(9)
H6A0.8116420.2880470.4782720.049*
H6B0.8112530.3562350.6185910.049*
H6C0.8583210.3926540.4565360.049*

Source of material

In a representative experiment 0.161 mL (0.162 g; 1 mmol) S-nicotine [(S)-3-[1-methylpyrrolidin-2-yl]pyridine; Acros Organics] were dissolved in a few drops of concentrated hydroiodic acid (Merck KGa). The hydroiodic acid was purified by a treatment with activated carbon to reduce the iodine concentration. To the aforementioned solution 0.319 g of ZnI2 (1 mmol; Aldrich) were added. This mixture was heated to 70 °C, giving an orange solution. Almost colourless crystals of the title compound were grown during storage in the refrigerator within a few days. MP. 224 °C.

Raman Spectrum. (Bruker MultiRam; resolution: 4 cm−1) [cm−1]: 3101(w), 3046(w), 3020(m), 2950(m, br), 2872(w), 1632(w), 1603(w), 1462(m, br), 1409(w), 1260(w), 1228(m), 1184(m), 1049(m), 1025(m), 967(w), 770(w), 614(w), 420(br, w), 255(w), 165(s, sh), 124(vs), 111 (vs), 81 (s), 72(s). IR Spectrum. (Perkin Elmer Frontier MIR; resolution: 4 cm−1) [cm−1]: 3204(s), 3162(vs), 3119(s), 3072(s), 3042(vs), 3016(s), 2965(vs), 2723(m), 1630(m), 1601(s), 1541(s), 1455(s, br), 1405(m), 1372(m), 1311(w), 1248(w), 1184(w), 1087(w), 1011(w), 983(m), 863(m), 788(s), 671(s).

Experimental details

Hydrogen atoms were placed using a riding model (AFIX 13/23/43/137) implemented in the SHELXL program system [3] using the standard parameters for constrained Uiso(H) values [3]. The absolute structure determination succeeded as the derived Flack parameter is found to be near zero with a low standard uncertainty [0.009(12) from 3488 selected quotients using Parsons’s method [5]]. The classical calculation of the Flack parameter showed a slightly worse result, 0.016(18) using all reflections [3], [5].

Comment

A recently performed Cambridge Structural Database [6] survey on nicotine-containing crystal structures yielded approximately fifty deposited structures. As reported and summarized by one of us [7] structural data are available for (a) metal complexes, which contain neutral nicotine ligands; (b) a small number of co-crystals containing neutral nicotine as one of the components; (c) some examples for pyrrolidinyl-monoprotonated nicotinium salts; and (d) mono-protonated nicotinium as a cationic ligand. As a result of the database survey specified above, only a limited number of examples of salt structures containing doubly protonated nicotinium cations have been reported so far [7], [8], [9], [10], [11], [12]. This contribution is part of our continuing interest in synthesis, characterization and understanding of hydrogen-bonding schemes of salts of natural products [7], [11], [12], [13], [14]. The choice of a [ZnI4]2− counter anion is part of our general interest in halogen bonding interactions between iodine containing molecules and ions, regardless of whether they are attractive or repulsive [15], [16], [17].

Description. The asymmetric unit of the title structure contains one 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium (nicotin-1,1′-dium) dication (nicH2) and one tetraiodidozincate(II) dianion. As discussed several times [7], [11], [12], the protonation at the nitrogen atom of the pyrrolinyl moiety creates a second chiral center at N1′ (cf. left part of the Figure), which shows R configuration in all reliable crystal structures deposited in the Cambridge Structural database so far. The four carbon atoms of the pyrrolidinyl moiety (C2′, C3′, C4′, C5′ ) are almost planar (RMS deviation = 0.07 Å) and the N1′ atom is folded out of this plane by 0.53(1) Å. The aforementioned plane defined by the carbon atoms C2′, C3′, C4′ & C5′ encloses an angle of 67.5(2)° with the mean plane of the pyridinyl moiety (see the Figure). The rotation around the C3—C2′ single bond causes a certain flexibility of the nicH2 dication and the final orientation is more or less a consequence of the packing and the hydrogen-bonding scheme, respectively. The bond lengths and angles within the nicH2 dication [7], [11], [12] as well as those in the [ZnI4]2− ion [18], [19], [20] are in the expected ranges. The Zn—I bond lengths of the complex [ZnI4]2− anion are: Zn1—I1 2.6298(4) Å, Zn1—I2 2.6117(4) Å, Zn1—I3 2.6109(4) Å and Zn1—I4 2.6176(4) Å. Small alterations of the Zn—I bond lengths are well known for hydrogen bonded [ZnI4]2− anion. [18], whereas in the case of a salt that doesn’t contain classical hydrogen bonds the Zn—I distances are almost equilibrated [19]. In the title structure the longest Zn—I bond length [Zn1—I1 2.6298(4) Å] correlates with the shortest hydrogen bond (see below).

The Raman spectrum (see the Source of materials section) supports the finding of a slightly distorted [ZnI4]2− anion. The assignment of the [ZnI4]2− anion-related Raman signals (80–300 cm−1) is in accord with the literature [20], [21], [22]. The symmetrical stretch mode (ν1) perfectly fits with a report of Lutz and Pfitzner [22]. The same is true for a shoulder at 165 cm−1, which can be assigned as ν3 [20]. The ν1 and ν4 modes are expected to appear between 40 and 60 cm−1. They can’t be assigned beyond doubt, as the spectral range of our spectrometer starts at 50 cm−1 and the two signals detected in this range are seriously shifted with respect to the expectation.

Supramolecular aspects. The nicH2 participates in one classical NH⋯I hydrogen bond between the methylpyrrolidin-1-ium-2-yl moiety and one iodido ligand of the complex [ZnI4]2− anion [N1′⋯I1 = 3.481(3) Å; H⋯I1 = 2.63 Å; cf. left part of the Figure]. The NH+ function of the pyridin-1-ium-3-yl moiety is located between the iodido ligands I2 and I4 of a neighboring [ZnI4]2− anion [N1⋯I2′ = 3.695(3) Å; N1⋯I4′ = 3.711(3); cf. right part of the Figure; ′ = 1 + x, y, −1 + z]. In this structure the NH+ function of the pyridin-1-ium-3-yl moiety forms a very weak hydrogen bond which is perhaps better described as a combined hydrogen bond/Coulomb-type/van-der-Waals type interaction [23]. Our classification is supported by the fact that two aromatic CH functions of the pyridin-1-ium-3-yl have C⋯I distances, which are almost in the same range [C6⋯I4′ = 3.711(4) Å; C2⋯I4′ 3.918(4) Å] as the aforementioned N1⋯I2′ and N1⋯I4′ distances.

Outlook. It may be of interest to test more nicotin-1,1′-dium tetrahalogenidometallate salts in catalysis as for other nicotin-1,1′-dium salts some catalytic properties are observed [24], [25].

Acknowledgements

We gratefully acknowledge support by the Ministry of Innovation, Science and Research of North-Rhine Westphalia and the German Research Foundation (DFG) for financial support (Xcalibur diffractometer; INST 208/533-1). We thank E. Hammes for the technical support (Raman and IR spectrum). Funding by the OPEN ACCESS fund of the Heinrich-Heine-Universität Düsseldorf is also gratefully acknowledged.

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Received: 2020-03-04
Accepted: 2020-04-23
Published Online: 2020-05-05
Published in Print: 2020-06-25

©2020 Guido J. Reiss 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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  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
https://doi.org/10.1515/ncrs-2020-0123
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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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