Home The crystal structure of 4,4′-bipyridinium bis-(2-hydroxy-3-methoxybenzoate), 2(C8H7.68O4)·C10H8.64N2
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The crystal structure of 4,4′-bipyridinium bis-(2-hydroxy-3-methoxybenzoate), 2(C8H7.68O4)·C10H8.64N2

  • Devin J. Angevine ORCID logo and Jason B. Benedict ORCID logo EMAIL logo
Published/Copyright: May 13, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 4

Abstract

C26H24N2O8, monoclinic, P21/c (no. 14), a = 6.9170(9) Å, b = 26.012(3) Å, c = 12.7449(17) Å, β = 91.896(4)°, V = 2291.9(5) Å3, Z = 4, Rgt(F) = 0.0471, wRref(F2) = 0.1320, T = 90 K.

CCDC no.: 2169893

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 plate
Size: 0.45 × 0.13 × 0.02 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.11 mm−1
Diffractometer, scan mode: Bruker Apex-II, φ and ω
θmax, completeness: 29.6°, >99%
N(hkl)measured, N(hkl)unique, Rint: 25,125, 6412, 0.071
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 4674
N(param)refined: 346
Programs: Bruker [1], Olex2 [2], Shelx [3]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.1488 (2) 0.33321 (5) 0.39798 (10) 0.0164 (3)
C2 0.32354 (19) 0.30060 (5) 0.39479 (10) 0.0147 (3)
C3 0.3691 (2) 0.27359 (5) 0.30307 (10) 0.0171 (3)
H3A 0.287959 0.275990 0.243602 0.021*
C4 0.5326 (2) 0.24373 (6) 0.30102 (11) 0.0187 (3)
H4 0.561497 0.225917 0.240237 0.022*
C5 0.6562 (2) 0.23995 (6) 0.39011 (11) 0.0181 (3)
H5A 0.767171 0.219828 0.388024 0.022*
C6 0.6139 (2) 0.26601 (5) 0.48102 (10) 0.0160 (3)
C7 0.4465 (2) 0.29675 (5) 0.48407 (10) 0.0154 (3)
C8 0.8782 (2) 0.22887 (6) 0.57887 (12) 0.0268 (3)
H8A 0.976734 0.238913 0.531699 0.040*
H8B 0.830637 0.195357 0.559851 0.040*
H8C 0.931471 0.228037 0.649353 0.040*
C9 0.5586 (2) 0.07387 (5) 0.31047 (11) 0.0170 (3)
C10 0.74424 (19) 0.10248 (5) 0.31791 (10) 0.0152 (3)
C11 0.8053 (2) 0.13242 (5) 0.23358 (10) 0.0159 (3)
H11 0.727475 0.135376 0.172947 0.019*
C12 0.9801 (2) 0.15734 (5) 0.24090 (11) 0.0177 (3)
H12 1.021426 0.176585 0.184377 0.021*
C13 1.0969 (2) 0.15412 (5) 0.33233 (11) 0.0183 (3)
H13 1.215866 0.170805 0.335830 0.022*
C14 1.0361 (2) 0.12618 (5) 0.41775 (11) 0.0170 (3)
C15 0.8597 (2) 0.09921 (5) 0.41040 (10) 0.0161 (3)
C16 1.3035 (2) 0.15430 (6) 0.52587 (13) 0.0253 (3)
H16A 1.347720 0.153616 0.598051 0.038*
H16B 1.272224 0.188975 0.505895 0.038*
H16C 1.403527 0.141496 0.482426 0.038*
C17 0.6459 (2) 0.40244 (5) 0.40800 (11) 0.0187 (3)
H17 0.700538 0.393133 0.472909 0.022*
C18 0.4767 (2) 0.43064 (6) 0.40500 (11) 0.0177 (3)
H18 0.418900 0.439987 0.467034 0.021*
C19 0.39245 (19) 0.44510 (5) 0.30780 (11) 0.0154 (3)
C20 0.4869 (2) 0.43039 (5) 0.21812 (11) 0.0176 (3)
H20 0.437275 0.439659 0.152091 0.021*
C21 0.6554 (2) 0.40184 (6) 0.22774 (11) 0.0192 (3)
H21 0.716340 0.391837 0.167081 0.023*
C22 0.20895 (19) 0.47480 (5) 0.29949 (11) 0.0151 (3)
C23 0.1542 (2) 0.50732 (5) 0.38053 (10) 0.0172 (3)
H23 0.232326 0.510615 0.440958 0.021*
C24 −0.0170 (2) 0.53456 (6) 0.37018 (11) 0.0183 (3)
H24 −0.052492 0.556019 0.424652 0.022*
C25 −0.0809 (2) 0.50091 (5) 0.20513 (11) 0.0189 (3)
H25 −0.160049 0.499230 0.144807 0.023*
C26 0.0876 (2) 0.47206 (5) 0.20979 (11) 0.0173 (3)
H26 0.119525 0.451094 0.153844 0.021*
H1Aa 0.844 (12) 0.373 (3) 0.314 (5) 0.040*
H1Bb −0.064 (6) 0.3530 (15) 0.318 (2) 0.040*
H2Bb 0.342 (6) 0.0588 (12) 0.227 (2) 0.031*
H2Aa −0.232 (13) 0.551 (3) 0.278 (5) 0.040*
N1 0.73415 (18) 0.38805 (5) 0.32100 (10) 0.0186 (3)
N2 −0.13397 (18) 0.53112 (5) 0.28421 (10) 0.0180 (2)
O1 0.04370 (16) 0.33450 (4) 0.31118 (8) 0.0234 (2)
O2 0.10698 (15) 0.35762 (4) 0.47794 (8) 0.0223 (2)
O3 0.41371 (16) 0.32155 (4) 0.57534 (8) 0.0228 (2)
H3 0.307 (3) 0.3391 (8) 0.5615 (14) 0.034*
O4 0.72337 (15) 0.26493 (4) 0.57248 (8) 0.0231 (2)
O5 0.46117 (15) 0.07778 (4) 0.22146 (8) 0.0205 (2)
O6 0.50174 (15) 0.04783 (4) 0.38533 (8) 0.0228 (2)
O7 0.80804 (16) 0.07094 (4) 0.49432 (8) 0.0222 (2)
H7 0.699 (3) 0.0567 (8) 0.4768 (15) 0.033*
O8 1.13486 (15) 0.12267 (4) 0.51279 (8) 0.0227 (2)

  1. aOccupancy: 0.32 (4), bOccupancy: 0.68 (4).

Source of material

4,4′-Bipyridine (156.2 mg, 1.0 mmol) and o-vanillic acid (168.1 mg, 1.0 mmol) were dissolved using excess methanol in a 200 mL beaker. The beaker was left open to allow for crystal formation upon slow evaporation. Coformers were sourced from Combi-Blocks (o-vanillic acid, 97% and 4,4′-bipyridine, 97%). Methanol was purchased from Fischer Chemical (HPLC grade; 99.9%). No further material refinement was necessary.

Experimental details

X-ray diffraction data was collected using a Bruker Smart Apex-II CCD diffractometer installed at a rotating anode source (MoKα radiation, λ = 0.71073 Å) and equipped with an Oxford Cryosystems (Cryostream700) nitrogen gas-flow apparatus. Five sets of data (290 frames each) were collected by the rotation method with 0.5° frame-width (ω scan). The sample was run at 90 K. Using Olex2, the structure was solved with intrinsic phasing via the ShelXT structure solution program and refined with the ShelXL software suite [2, 3]. The atomic coordinates of H atoms attached to heteroatoms were freely refined with thermal parameters constrained to be Uiso(H) = 1.5Ueq(N) or 1.5Ueq(O). H atoms connected to carbon atoms were placed geometrically (C–H = 0.95 Å) and refined with thermal parameters constrained to be Uiso(H) = 1.2Ueq(C). The disordered protons were initially refined independently, however given the similar refined occupancies the disorder was ultimately modeled as correlated using a single occupancy parameter (Table 2).

Comment

2-Hydroxy-3-methoxybenzoic acid, known commonly as o-vanillic acid, has been under investigation for its medicinal benefits such as its anti-allergenic inflammatory response [4]. Despite the rise in interest and utility of this molecule, only a handful of crystal structures containing o-vanillic acid have been reported [5], [6], [7]. As such additional co-crystals and/or salts of o-vanillic acid may aid in further understanding its solid-state interactions. In this report the coformer 4,4′-bipyridine (4,4′-BIPY) was selected due to its ability to form a variety of crystalline systems including metal-organic frameworks, co-crystals, and salts [8], [9], [10].

o-Vanillic acid co-crystallizes with 4,4′-BIPY in a 2:1 ratio in the monoclinic spacegroup (P21/c). Subsequent refinements revealed the presence of disorder involving the acidic protons of the carboxylic acid groups of the vanillic acid and the pyridyl groups of the 4,4′-BIPY. For each of the two crystallographically unique acid groups, the proton was disordered over two positions. In one case, the proton was located near the oxygen, and in the second case the proton was located near the nitrogen of the pyridyl group. The ratio of the occupancies (HO:HN) of the disordered protons when refined independently were determined to be 0.68225:0.31775 and 0.68721:0.31279. Given the similar values, the occupancies were treated with a single parameter in the final model and determined to be 0.68(4):0.32(4).

These values may be interpreted as a partial charge transfer with the proton being transferred to the nitrogen resulting in a salt 32(4)% of the time. The other 68(4)% of the time, the protons reside on the acid oxygen resulting in charge neutral carboxylic acid and pyridyl groups. The two acids and the 4,4′-BIPY together form discrete hydrogen bonded trimolecular assemblies. These assemblies form slipped stacks through π–π interactions approximately along [100]. Lateral Van der Waals interatactions approximately along [001] give rise to 2-D sheets. These sheets form alternating layers along [010] in which each layer is rotated by 180°.

Corresponding author: Jason B. Benedict, Department of Chemistry, The State University of New York at Buffalo, Buffalo, NY 14260-3000, USA, E-mail:

Funding source: National Science Foundation

Award Identifier / Grant number: DMR-2003932

Acknowledgements

Funding for this research was provided by: National Science Foundation, Directorate for Mathematical and Physical Sciences (award No. DMR-2003932).

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: National Science Foundation, Directorate for Mathematical and Physical Sciences (award No. DMR-2003932).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. BRUKER. SAINT, APEX2 and SADABS. Bruker AXS Inc.: Madison, Wisconsin, USA, 2009.Search in Google Scholar

2. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. Olex2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

3. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122; https://doi.org/10.1107/s0108767307043930.Search in Google Scholar PubMed

4. Kim, M. C., Kim, S. J., Kim, D. S., Jeon, Y. D., Park, S. J., Lee, H. S., Um, J. Y., Hong, S. H. Vanillic acid inhibits inflammatory mediators by suppressing NF-κB in lipopolysaccharide-stimulated mouse peritoneal macrophages. Immunopharmacol. Immunotoxicol. 2011, 33, 525–532; https://doi.org/10.3109/08923973.2010.547500.Search in Google Scholar PubMed

5. Fang, Z.-Q., Zeng, R.-H., Yang, M., Liu, H., Chen, X.-L. 2-Hydroxy-3-methoxybenzoic acid monohydrate. Acta Crystallogr. 2008, E64, o691; https://doi.org/10.1107/s1600536808006065.Search in Google Scholar

6. Liu, Z.-H., Qiu, Y.-C., Li, Y.-H., Zeng, R.-H., Deng, H. 2-Hydroxy-3-methoxybenzoic acid. Acta Crystallogr. 2007, E63, o2616–o2617; https://doi.org/10.1107/s1600536807018739.Search in Google Scholar

7. Fronczek, F. R. CCDC 1525788: Experimental Crystal Structure Determination; Cambridge Crystallographic Data Centre: Cambridge, United Kingdom, 2017.Search in Google Scholar

8. Walton, I. M., Cox, J. M., Myers, S. D., Benson, C. A., Mitchell, T. B., Bateman, G. S., Sylvester, E. D., Chen, Y.-S., Benedict, J. B. Determination of the dehydration pathway in a flexible metal-organic framework by dynamic in situ x-ray diffraction. Struct. Dyn. 2020, 7, 034305; https://doi.org/10.1063/4.0000015.Search in Google Scholar PubMed PubMed Central

9. Mudsainiyan, R. K., Jassal, A. K., Pandey, S. K. Structural diversity from co-crystal to 1D coordination polymers of 2,6-naphthalenedicarboxylic acid with 4,4′-bipyridine as coligand: structural and computational approach. J. Coord. Chem. 2020, 73, 3363–3381; https://doi.org/10.1080/00958972.2020.1853108.Search in Google Scholar

10. Sylvester, E., McGovern, M., Young Lee, A., Nguyen, P., Park, J., Benedict, J. B. Partial charge transfer in the salt co-crystal of l-ascorbic acid and 4,4′-bi-pyridine. Acta Crystallogr. 2019, E75, 728–731; https://doi.org/10.1107/s2056989019005334.Search in Google Scholar
Received: 2022-03-15
Accepted: 2022-05-02
Published Online: 2022-05-13
Published in Print: 2022-08-26

© 2022 Devin J. Angevine and Jason B. Benedict, published by De Gruyter, Berlin/Boston

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

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  68. Crystal structure of 3-(3-bromophenyl)-1′,3′-dimethyl-2′H,3H,4H-spiro[furo[3, 2-c]chromene-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H) tetraone, C22H15BrN2O6
  69. The crystal structure of poly[aqua-(μ2-4,4′- bis(imidazolyl)biphenyl-κ2N:N′)-(μ2-3-nitrobenzene-1,2-dicarboxylato-κ2O:O′)]copper (II) hydrate, C26H21N5O8Cu
  70. The crystal structure of bis(4-(6-carboxy-8-ethyl-3-fluoro-5-oxo-5,8-dihydro-1,8-naphthyridin-2- yl)piperazin-1-ium) adipate tetrahydrate, C36H52F2N8O14
  71. Synthesis and crystal structure of poly[aqua(μ4-(1R,2S,4R)-4-hydroxy-1-((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)pyrrolidin-1-ium-2-carboxylate-κ4O:O′:O″:O‴)sodium(I)] monohydrate, C21H22NNaO12S
  72. Crystal structure of chlorido-(η6-toluene)(2,2′-bipyridine-κ2N,N′)ruthenium(II) hexafluorophosphate, C17H16ClN2RuPF6
  73. The crystal structure of (R)-6-hydroxy-8-methoxy-3-methylisochroman-1-one, C11H12O4
  74. Crystal structure of catena-poly[(5,5,7,12,12,14-hexamethyl -1,4,8,11-tetraazacyclotetradecane- κ4N,N′,Nʺ,N‴)nickel(II)-(μ2-perchlorato-κ2O:O′)] 3,5-dicarboxybenzoate – methanol (1/2), C27H49ClN4NiO12
  75. The crystal structure of 4-(chloromethyl)benzonitrile, C8H6ClN
  76. The crystal structure of dimethylammonium 8-[(7,9-dioxo-6,10-dioxaspiro[4.5]decan-8-ylidene)methyl]-9-oxo-6,10-dioxaspiro[4.5]dec-7-en-7-olate, C19H25NO8
  77. Crystal structure of (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((1-acetyl-5-bromo-4-chloro-1H-indol-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate hemihydrate C24H25BrClNO11
  78. The crystal structure of the co-crystal tetrakis[2-(tris(4-methoxyphenyl)stannyl)ethyl]silane – tetrahydrofuran – toluene – tetrahydrofurane (1/1/1), C103H116O13SiSn4
  79. Crystal structure of methyl 3-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoate, C16H13NO4
  80. Crystal structure of ethyl (Z)-3-amino-2-cyano-3-(2-oxo-2H-chromen-3-yl)acrylate, C15H12N2O4
  81. Crystal structure of methyl 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetate, C15H11NO4
  82. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)cobalt(II)] tetrafluoroterephthalate, C26H28N8O6F4Co
https://doi.org/10.1515/ncrs-2022-0126
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of N-((3s,5s,7s)-adamantan-1-yl)-2-(3-benzoylphenyl)propanamide, C26H29NO2
  4. The crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxidopropylidene)benzohydrazonato-κ5 N,O,O′:N′,O′′)-octakis(pyridine-κ1 N)trinickel(II) C60H56Cl2N12Ni3O6
  5. The crystal structure of 3-(4-chlorophenyl)-1,5-di-p-tolylpentane-1,5-dione, C25H23ClO2
  6. The crystal structure of 2,4,4-triphenyl-4H-benzo[b][1,4]oxaphosphinin-4-ium bromide – dichloromethane (1/1), C27H22BrCl2OP
  7. The crystal structure of 2-(3,6-di-tert-butyl-1,8-diiodo-9H-carbazol-9-yl)acetonitrile, C22H24I2N2
  8. Crystal structure of 3-phenylpropyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O3
  9. The crystal structure of (4-fluorophenyl)(5-(hydroxymethyl)furan-2-yl)methanol, C12H11FO3
  10. Crystal structure of the dihydrate of tetraethylammonium 1,3,5-thiadiazole-5-amido-2-carbamate, C11H27N5O4S
  11. Crystal structure of (Z)-4-[(p-tolylamino)(furan-2-yl)methylene]-3-phenyl-1-1-p-tolyl-1H-phenyl-1H-pyrazol-5(4H)-one, C28H23N3O2
  12. The crystal structure of (E)-3-(2-chlorophenyl)-1-ferrocenylprop-2-en-1-one, C19H15ClFeO
  13. The pseudosymmetric crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium hexachloridostannate(IV), C10H16N2SnCl6
  14. Crystal structure of (2-(1-hydroxyheptyl)octahydro-8aH-chromene-5,8,8a-triol), C16H30O5
  15. The crystal structure of N-cyclohexyl-3-hydroxy-4-methoxybenzamide, C14H19NO3
  16. Crystal structure of 1-(4-hydroxybenzyl)-4-methoxy-9,10-dihydrophenanthrene-2,7-diol from Arundina graminifolia, C22H20O4
  17. The crystal structure of N-cyclopentyl-3-hydroxy-4-methoxybenzamide, C13H17NO3
  18. The crystal structure of 2,5,5-triphenyl-3,5-dihydro-4H-imidazol-4-one, C21H16N2O
  19. Crystal structure of 1H-1,2,3-Triazolo[4,5-b]-pyridin-4-ium nitrate, C5H5N5O3
  20. Crystal structure of (Z)-4-(((4-bromophenyl)amino)(furan-2-yl)methylene)-2,5-diphenyl-2,4-dihydro-3H-pyrazol-3-one, C26H18BrN3O2
  21. Crystal structure of 2-(4-methoxyphenyl)-3-methyl-1,8-naphthyridine, C16H14N2O
  22. The crystal structure of 3-([1,1′-biphenyl]-2-yl)-1,2-diphenylbenzo[b]phosphole-1-oxide, C32H23OP
  23. The crystal structure of ammonium (E)-4-((4-carboxyphenyl)diazenyl)benzoate, C14H13N3O4
  24. Crystal structure of bis(5-amino-1,2,4-triazol-4-ium-3-yl)methane sulfate, C5H10N8O4S
  25. The crystal structure of phenantroline-κ2 N,N′-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)copper(II), C36H24N4O4Cu
  26. The crystal structure of tris(6-methylpyridin-2-yl)phosphine oxide, C18H18N3OP
  27. The crystal structure of N-(2′-hydroxymethyl-5′-phenyl-3′,4′-dihydro-[1,1′:3′,1″-terphenyl]- 1′(2′H)-yl)-P,P-diphenylphosphinic amide, C37H34NO2P
  28. Crystal structure of (E)-4-(6-(4-(2-(pyridin-4-yl)vinyl)phenoxy)pyrimidin-4-yl)morpholine, C21H20N4O2
  29. Crystal structure of 5-(adamantan-1-yl)-3-[(4-trifluoromethylanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, C20H22F3N3OS
  30. Crystal structure of 2,2-dichloro-1-(4-chloro-1H-indol-1-yl)ethan-1-one, C10H6Cl3NO
  31. The crystal structure of 4-(((3-bromo-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)benzonitrile, C28H16Br2F6N4O2
  32. The crystal structure of 1H-benzimidazole-2-carboxamide, C8H7N3O
  33. The crystal structure of Histidinium hydrogensquarate, C10H11N3O6
  34. The crystal structure of 3-amino-5-carboxypyridin-1-ium iodide, C6H7IN2O2
  35. Crystal structure of (E)-amino(2-(3-ethoxy-4-hydroxybenzylidene)hydrazineyl)methaniminium nitrate hemihydrate C10H16N5O5.5
  36. Crystal structure of 1,2-bis(4,5-dinitro-1H-imidazol-1-yl)ethane, C8H6N8O8
  37. The crystal structure of diaqua-bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2N,O)manganese(II), C14H12N6O6Mn
  38. The crystal structure of catena-poly[aqua-2,2′bipyridine-κ2N,N′-(μ2-5-ethoxyisophthalato-κ 4O,O′:Oʺ,O′ʺ)cadmium(II)] monohydrate, C20H20CdN2O7
  39. The crystal structure of (1S,3R)-1-(4-isopropylphenyl)-3-(methoxycarbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-iumchloride monohydrate, C22H27ClN2O3
  40. Crystal structure of 1-isopropyl-3-(prop-1-en-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, C11H15N5
  41. The crystal structure of (2,2′-bipyridine-κ2N,N′)- bis(6-phenylpyridine-2-carboxylate-κ2N,O)manganese(II)] monohydrate, C34H26N4O5Mn
  42. Crystal structure of the cocrystal 1,3,5,7-tetranitro-1,3,5,7-tetrazoctane ─ 2,3-dihydroindole (1/1), C12H17N9O8
  43. Crystal structure of 3-acetyl-6-hydroxy-2H-chromen-2-one monohydrate, C11H10O5
  44. Crystal structure of 6,9-diamino-2-ethoxyacridinium 3,5-dinitrobenozate — dimethylsulfoxide — water (1/1/1), C24H27N5O9S
  45. The crystal structure of 4,4′-bipyridinium bis-(2-hydroxy-3-methoxybenzoate), 2(C8H7.68O4)·C10H8.64N2
  46. Crystal structure of (Z)-4-(((4-fluorophenyl)amino)(furan-2-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
  47. The crystal structure of bis(4-chloro-2-(((2-chloroethyl)imino)methyl)phenolato-κ2N,O)-oxidovanadium(IV), C18H16Cl4N2O3V
  48. The crystal structure of 17-(bromoethynyl)-17-hydroxy-10, 13-dimethyl- 1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one, C21H27BrO2
  49. The crystal structure of 4-((6-fluoropyridin-2-yloxy)methyl)benzonitrile, C13H9FN2O
  50. Crystal structure of (Z)-2-(1-bromo-2-phenylvinyl)-5-ethyl-2-methyl-1,3-dioxane-5-carboxylic acid, C15H17Br1O4
  51. Crystal structure of catena-poly[tribenzyl-κ1C-(μ2-6-oxidopyridin-1-ium-3-carboxylato-κ2O:O’)tin(IV)-dichloromethane-methanol (1/1/1), C29H31Cl2NO4Sn
  52. Crystal structure of bis{2-(tert-butyl)-6-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}zinc(II), C40H46N4O4Zn
  53. Crystal structure of diaqua-bis(μ2-2-carboxy-3,4,5,6-tetrafluorobenzoato-κ2O:O′)-bis(phenanthroline-κ2N,N′)-bis(μ2-3,4,5,6-tetrafluorophthalato-κ3O:O,O′)dieuropium(III) – phenanthroline (1/2), C40H19EuF8N4O9
  54. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2N,O) manganese(II) — water — dimethylformamide (1/2/1), C27H31N3O9Mn
  55. The crystal structure of bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2N,O)-copper(ii), C14H8N6O4Cu
  56. Crystal structure of poly[(μ2-1-(1-imidazolyl)-4-(imidazol-1-ylmethyl)benzene-κ2N:N′)-(μ3-pyridazine-4,5-dicarboxylate-κ3O:O′:N)]copper(II) hydrate, C19H16CuN6O5
  57. Crystal structure of acrinidinium tetrafluorohydrogenphthalate, C21H11F4NO4
  58. Crystal structure of 2-(1H-pyrazol-3-yl-κN)pyridine-κN-bis(2-(2,4-difluorophenyl)pyridinato-κ2C,N)iridium(III) sesquihydrate, C30H18F4IrN5·1.5[H2O]
  59. Crystal structure of 2-(2-hydroxy-5-nitrophenyl)-5-methyl-1,3-dioxane-5-carboxylic acid, C12H13N1O7
  60. The crystal structure of 1,2-bis(pyridinium-4-yl)ethane diperchlorate, C12H14N2·2ClO4 – a second polymorph
  61. The crystal structure of [(1,10-phenantroline-κ2N,N′)-bis(6-phenylpyridine-2-carboxylato-κ2N,O)manganese(II)] monohydrate, C36H26N4O5Mn
  62. Crystal structure of 1,2-bis(2,2,3,3,5,5,5-heptamethyl-1,1,4,4- tetrakis(trimethylsilyl)pentasilan-1-yl)ditellane, C38H114Si18Te2
  63. Crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane – dimethylformamide (1/1), C11H13N9O9
  64. Crystal structure of (Z)-3-((tert-butylamino) methylene)-2-(2-hydroxynaphthalen-1-yl) chroman-4-one, C24H23NO3
  65. Synthesis and crystal structure of (E)-1-(4-(((E)-3-(tert-butyl)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-ethyl oxime, C21H26N2O2
  66. Crystal structure of the double salt bis(5-amino-1,2,4-triazol-4-ium-3-yl)methane hydrogen oxalate hemioxalate, C8H11N8O6
  67. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-[(4-pyridinylmethyl)amino]benzoato-κ2N:O)cobalt(II)]–1,2bi(4-pyridyl)ethene–water (1/1/1), C50H50N8O8Co
  68. Crystal structure of 3-(3-bromophenyl)-1′,3′-dimethyl-2′H,3H,4H-spiro[furo[3, 2-c]chromene-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H) tetraone, C22H15BrN2O6
  69. The crystal structure of poly[aqua-(μ2-4,4′- bis(imidazolyl)biphenyl-κ2N:N′)-(μ2-3-nitrobenzene-1,2-dicarboxylato-κ2O:O′)]copper (II) hydrate, C26H21N5O8Cu
  70. The crystal structure of bis(4-(6-carboxy-8-ethyl-3-fluoro-5-oxo-5,8-dihydro-1,8-naphthyridin-2- yl)piperazin-1-ium) adipate tetrahydrate, C36H52F2N8O14
  71. Synthesis and crystal structure of poly[aqua(μ4-(1R,2S,4R)-4-hydroxy-1-((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)pyrrolidin-1-ium-2-carboxylate-κ4O:O′:O″:O‴)sodium(I)] monohydrate, C21H22NNaO12S
  72. Crystal structure of chlorido-(η6-toluene)(2,2′-bipyridine-κ2N,N′)ruthenium(II) hexafluorophosphate, C17H16ClN2RuPF6
  73. The crystal structure of (R)-6-hydroxy-8-methoxy-3-methylisochroman-1-one, C11H12O4
  74. Crystal structure of catena-poly[(5,5,7,12,12,14-hexamethyl -1,4,8,11-tetraazacyclotetradecane- κ4N,N′,Nʺ,N‴)nickel(II)-(μ2-perchlorato-κ2O:O′)] 3,5-dicarboxybenzoate – methanol (1/2), C27H49ClN4NiO12
  75. The crystal structure of 4-(chloromethyl)benzonitrile, C8H6ClN
  76. The crystal structure of dimethylammonium 8-[(7,9-dioxo-6,10-dioxaspiro[4.5]decan-8-ylidene)methyl]-9-oxo-6,10-dioxaspiro[4.5]dec-7-en-7-olate, C19H25NO8
  77. Crystal structure of (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((1-acetyl-5-bromo-4-chloro-1H-indol-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate hemihydrate C24H25BrClNO11
  78. The crystal structure of the co-crystal tetrakis[2-(tris(4-methoxyphenyl)stannyl)ethyl]silane – tetrahydrofuran – toluene – tetrahydrofurane (1/1/1), C103H116O13SiSn4
  79. Crystal structure of methyl 3-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoate, C16H13NO4
  80. Crystal structure of ethyl (Z)-3-amino-2-cyano-3-(2-oxo-2H-chromen-3-yl)acrylate, C15H12N2O4
  81. Crystal structure of methyl 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetate, C15H11NO4
  82. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)cobalt(II)] tetrafluoroterephthalate, C26H28N8O6F4Co
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