Home Crystal structure of 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one, C12H9FO3
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Crystal structure of 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one, C12H9FO3

  • Grace Obi , Sizwe J. Zamisa ORCID logo EMAIL logo and Fanie R. van Heerden
Published/Copyright: December 5, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 2

Abstract

C12H9FO3, triclinic, P1̄ (no. 2), a = 7.1983(6) Å, b = 7.3732(6) Å, c = 9.6439(8) Å, α = 81.489(5)°, β = 88.634(4)°, γ = 71.065(4)°, V = 478.66(7) Å3, Z = 2, Rgt(F2) = 0.0362, wRref(F2) = 0.1015, T = 100(2) K.

CCDC no.: 1964527

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 Rod
Size:0.50 × 0.19 × 0.16 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.12 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:27.4°, 98%
N(hkl)measured, N(hkl)unique, Rint:8040, 2142, 0.018
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1942
N(param)refined:146
Programs:Bruker [1], SHELX [2], [3], Mercury [4]
Table 2:

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

AtomxyzUiso*/Ueq
F10.34170(12)0.79159(12)0.91465(8)0.0224(2)
O10.31232(14)0.06558(13)0.28267(9)0.0165(2)
O20.12032(13)0.63559(12)0.33314(9)0.0147(2)
O3−0.02087(15)0.73199(13)0.12224(10)0.0207(2)
C10.2746(2)0.00563(18)0.15319(13)0.0180(3)
H1A0.1325690.0479850.1343220.027*
H1B0.328030−0.1359390.1613020.027*
H1C0.3375130.0641820.0760820.027*
C20.24409(18)0.25668(17)0.28849(13)0.0130(2)
C30.28477(18)0.30711(17)0.41944(12)0.0134(3)
H30.3545910.2094690.4927740.016*
C40.22279(18)0.49457(17)0.43721(12)0.0123(2)
C50.25280(17)0.57338(17)0.56325(12)0.0125(2)
C60.19936(18)0.77347(18)0.56231(13)0.0145(3)
H60.1432430.8591980.4793710.017*
C70.22719(19)0.84865(18)0.68094(13)0.0161(3)
H70.1899960.9846710.6806820.019*
C80.31034(19)0.72021(19)0.79907(13)0.0155(3)
C90.33530(19)0.44896(18)0.68597(13)0.0150(3)
H90.3717530.3127070.6877390.018*
C100.36460(19)0.52178(19)0.80508(13)0.0165(3)
H100.4205310.4373360.8885730.020*
C110.07485(19)0.59398(18)0.20336(12)0.0147(3)
C120.14505(18)0.39537(18)0.18272(12)0.0144(3)
H120.1225690.3603130.0952640.017*

Source of material

The dianion of ethyl acetoacetate (1.83 g, 14.04 mmol) was formed by the sequential treatment of the parent compound in THF (60 mL) with NaH (60% dispersion in mineral oil, 1.12 g, 28.0 mmol) and n-butyllithium (2.5 M in hexane, 9.2 mL, 23.20 mmol). Addition of ethyl 4-fluorobenzoate (2.36 g, 14.04 mmol) to the reaction mixture yielded ethyl (Z)-5-(4-fluorophenyl)-5-hydroxy-3-oxopent-4-enoate. Refluxing of ethyl (Z)-5-(4-fluorophenyl)-5-hydroxy-3-oxopent-4-enoate (0.23 g, 0.9 mmol) and 1,8-diazobicyclo[5.4.0]undecan-7-ene (DBU, 0.16 g, 1.0 mmol) in benzene (5 mL) overnight, according to the method described by Cervello et al. [5], led to base-mediated cyclization to yield 6-(4-fluorophenyl)-4-hydroxy-2H-pyran-2-one. Methylation of the product (0.41 g, 2.0 mmol) with dimethyl sulfate (0.38 g, 3.0 mmol) in the presence of potassium carbonate (0.8 g, 6.0 mmol) afforded the product 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one. Crystals were obtained by hot recrystallization using methanol. Yield = 97%, m.p. 202–206 °C. 1H NMR (400 MHz, CDCl3) δ [ppm] = 7.80 (ddd, 2H, J = 7.1, 5.2, 2.1 Hz), 7.13 (t, 2H, J = 8.7), 6.35 (d, 1H, J = 2.1 Hz), 5.53 (d, 1H, J = 2.1 Hz), 3.85 (s, 3H, OCH3). 13C NMR (400 MHz, CDCl3) δ [ppm] = 171.4, 164.5 (d, J = 252.4 Hz), 164.1, 159.4, 128.0 (d, J = 8.7 Hz), 127.5 (d, J = 3.5 Hz), 116.2 (d, J = 22.1 Hz), 97.9 (d, J = 1.1 Hz), 88.5, 56.2 (OCH3). 19F NMR (400 MHz, CDCl3) δ [ppm] = −108.50 (m). HRMS-ESI(+) calcd. for C12H9FO3Na [M+Na]+ 243.0433, found 243.0433. IR (neat) (cm−1) = 1727, 1265, 1217, 1165, 1069, 1008, 839, 797.

Experimental details

The visual crystal structure information was performed using Mercury [4] system software. All C—Haromatic, C—Hmethyl and C—Hmethylene bond distances were restrained to 0.95 Å, 0.98 Å and 0.99 Å with Uiso(Haromatic and Hmethylene) = 1.2Ueq and Uiso(Hmethyl) = 1.5Ueq of parent atom, respectively.

Comment

Many biologically active compounds containing a 2-pyrone moiety are known [6]. These compounds and synthetic analogues are associated with a diverse range of biological activities such as antiviral [7], anti-malarial, and anti-tuberculosis activities [8], hence there is an ongoing interest in the synthesis of these compounds. Several studies have shown that the incorporation of fluorine in molecules are likely to enhance the biological activities [9], which stimulated our interest in the synthesis of fluorinated 2-pyrones [10].

The crystal structure of the title compound has one molecular unit consisting of 4-fluorophenyl and pyrone moieties. Compared to the non-fluorinated molecule, the presence of the fluorine atom decreased the dihedral angle between the 4-fluorophenyl and pyrone rings from 8.8° to 7.2° [11]. Furthermore, the methoxy group was found to be more co-planar with the pyrone ring given a C1—O1—C2—C12 torsion angle of −0.5° compared to that observed in the non-fluorinated derivative [11]. Non-classical intermolecular C12—H12⋯O3 (symmetry code: −x, 1 − y, −z) and C10—H10⋯F1 (symmetry code: 1 − x, 1 − y, 2 − z) hydrogen bonds form alternating eight-membered rings with two donor atoms and an acceptor. These hydrogen bonding patterns link neighbouring molecules to form a one-dimensional supramolecular structure.

Acknowledgements

This work was supported by the University of KwaZulu-Natal and the National Research Foundation of South Africa (NRF) (Grant No: 98345, 2018).

References

1. Bruker. APEXII. Bruker AXS Inc., Madison, WI, USA (2009)Search in Google Scholar

2. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar

3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar

4. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A.: Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures. J. Appl. Crystallogr. 41 (2008) 466–470.10.1107/S0021889807067908Search in Google Scholar

5. Cervello, J.; Marquet, J.; Moreno-Mañas, M.: Copper and cobalt mediated regioselective alkylation of polyketide models: methyl 3,5-dioxohexanoate and triacetic acid lactone. Tetrahedron 46 (1990) 2035–2046.10.1016/S0040-4020(01)89770-2Search in Google Scholar

6. McGlacken, G. P.; Fairlamb, I. J.: 2-Pyrone natural products and mimetics: isolation, characterisation and biological activity. Nat. Prod. Rep. 22 (2005) 369–385.10.1039/b416651pSearch in Google Scholar PubMed

7. Defant, A.; Mancini, I.; Tomazzolli, R.; Balzarini, J.: Design, synthesis, and biological evaluation of novel 2H–pyran–2–one derivatives as potential HIV–1 reverse transcriptase inhibitors. Arch. Pharm. 348 (2015) 23–33.10.1002/ardp.201400235Search in Google Scholar PubMed

8. McCracken, S. T.; Kaiser, M.; Boshoff, H. I.; Boyd, P. D.; Copp, B. R.: Synthesis and antimalarial and antituberculosis activities of a series of natural and unnatural 4-methoxy-6-styryl-pyran-2-ones, dihydro analogues and photo-dimers. Bioorg. Med. Chem. 20 (2012) 1482–1493.10.1016/j.bmc.2011.12.053Search in Google Scholar PubMed PubMed Central

9. Hagmann, W. K.: The many roles for fluorine in medicinal chemistry. J. Med. Chem. 51 (2008) 4359–4369.10.1021/jm800219fSearch in Google Scholar PubMed

10. Obi, G.; Van Heerden, F. R.: Synthesis of 5,6-dehydrokawain and some fluorinated analogues. Synth. Commun. 48 (2018) 1482–1486.10.1080/00397911.2018.1455212Search in Google Scholar

11. Obi, G.; Zamisa, S. J.; Van Heerden, F. R.: Crystal structure of 4-methoxy-6-phenyl-2H-pyran-2-one, C12H10O3. Z. Kristallogr. NCS 233 (2018) 343–344.10.1515/ncrs-2017-0068Search in Google Scholar

Received: 2019-10-10
Accepted: 2019-11-08
Published Online: 2019-12-05
Published in Print: 2020-02-25

©2019 Grace Obi 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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  67. Crystal structure of (E)-2-cyano-N′-(1-(3-ethylpyrazin-2-yl)ethylidene)acetohydrazide, C11H3N5O
  68. Crystal structure of (2,7-dihexyl-9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane), C51H56OP2
  69. Crystal structure of 5-((bis(pyridin-2-ylmethyl)amino)methyl)quinolin-8-ol, C22H20N4O
  70. Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
  71. The crystal structure of [(tetra-μ2-2,6-difluorobenzoato-κ2O:O′)-bis-(2,6-difluorobenzoato-κ2O:O′)-bis-(1,10-phenanthroline-κ2N:N′)]dierbium(III) C66H34N4O12F12Er2
  72. Crystal structure of bis(3-chloro-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-k3N,N′,O)nickel(II), C26H20N8O2Cl2Ni
  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
https://doi.org/10.1515/ncrs-2019-0752
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Articles in the same Issue

  1. Frontmatter
  2. Synthesis and crystal structure of bis{5-fluorine-2-(((4-(1-(methoxy-imino)ethyl)phenyl) imino)methyl)phenolato-κ2N,O}copper(II), C32H28CuF2N4O4
  3. Redetermination of the crystal structure of N′-(3-ethoxy-2-hydroxybenzylidene)-4-fluorobenzohydrazide monohydrate, C16H17FN2O4
  4. The crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl) ethylidene)-2-hydroxybenzohydrazide, C15H12ClFN2O2
  5. Crystal structure of (E)-N-[4-(1H)-imidazolyl phenyl]-(2-methylphenyl)methanimine, C17H15N3
  6. The crystal structure of 1-benzyl-4-(2-(phenylethynyl)phenyl)-1H-1,2,3-triazole, C23H17N3
  7. Crystal structure of catena-poly[{μ2-1,5-bis(diphenylphosphanyl)pentane-κ2P:P′}dichloridocadmium(II)], C29H30CdCl2P2
  8. Crystal structure of methyl (E)-N2-((3-methylquinolin-8-yl)sulfonyl)-Nω′-nitro-L-argininate - ethanol (1/1), C19H28N6O7S
  9. The crystal structure of trans-carbonyl-(diphenylcyclohexyl-phosphine-κP)iodidomethyl-(2-oxopyridin-1(2H)-olato-κ2O,O′)rhodium(III), C25H28INO3PRh
  10. Crystal structure of N-(amino(pyrazin-2-yl)methylene)-6-methylpyridin-1-ium-3-carbohydrazonate-κ3O,N,N′)-(dinitrato-κ1O)zinc(II), C12H12N8O7Zn
  11. The crystal structure of dichlorido-(tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′)chromium(III) chloride — methanol (1/3), CrC27H33Cl3N7O3
  12. Crystal structure of catena-poly[aqua(μ4-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ8O,O′:O′,N:N′,O′′:O′′,O′′′))silver(I)], C10H24Ag2N2O10S2
  13. Crystal structure of bis(μ3-oxido)-bis(μ2–2,3,4,5-tetrafluorobenzoato-κ2O:O′)-bis(2,3,4,5-tetrafluorobenzoato-κO)-oktakis(3-chlorobenzyl-κC)tetratin(IV), C84H52Cl8F16O10Sn4
  14. Crystal structure of (E)-1-{4-[(4-fluoro-2-hydroxybenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15FN2O2
  15. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-N,N′)zinc(II)], {C20H30N4O4P2S4Zn}n
  16. Crystal structure of methyl 2-(4-(3-iodopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C15H12IN3O2
  17. Crystal structure of hexacarbonyl-(μ2-methanoato-k2O:O′)-(μ2–bis(di-p-tolylphosphino)cyclohexylamine-κ2P:P′)dirhenium(I), C42H45NO8P2Re2
  18. The cocrystal structure of 1′-hydroxy-1H,1′H-[5,5′-bitetrazol]-1-olate and 1,10-phenanthrolin-1-ium, C14H10N10O2
  19. The crystal structure of 1-benzyl-2-((4-(tert-butyl)phenyl)ethynyl)pyridin-1-ium bromide,C24H24BrN
  20. Crystal structure of (5,5′-bitetrazole-1,1′-diolate)-bis(1,10-phenanthroline)-copper(II), C26H16CuN12O2
  21. Crystal structure of bis(ammonium) diaqua-tetrakis(4-hydroxybenzoato)-manganese(II) tetrahydrate, [NH4]2[C28H24MnO14] ⋅ 4(H2O)
  22. The crystal structure of 3-chloro-1-hydrazino-2,4,6-trinitrobenzene, C6H4ClN5O6
  23. Crystal structure of catena-[(μ2-pyrazine-κ2N:N′)-bis(O,O′-di-ethyldithiophosphato-κ2S,S′)cadmium(II)], {C12H24CdN2O4P2S4}n
  24. Crystal structure of catena-poly[(μ2-pyrazine-N,N′)-bis(O,O′-di-isopropyldithiophosphato-S,S′)cadmium(II) acetonitrile di-solvate], [C16H32CdN2O4P2S4⋅2(C2H3N)]n
  25. Crystal structure of catena-poly{(μ2-N1,N2-bis[(pyridin-4-yl)methyl]ethanediamide-κ2N:N′)-bis(O,O′-di-isopropyldithiophosphato-κ1S)zinc(II)} — acetonitrile (1/1), C26H42N4O6P2S4Zn⋅C2H3N
  26. Crystal structure of tetraqua-bis(4-(hydroxymethyl)benzoato-κO)cobalt(II), C16H22O10Co
  27. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(4-pyridylmethylene)hydrazine-N,N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  28. Crystal structure of catena-poly[(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)-bis(O,O′-dimethyl dithiophosphato-κ2-S,S′)cadmium(II)], {C16H22CdN4O4P2S4}n
  29. Crystal structure of catena-poly[(bis(O,O′-diethyl dithiophosphato-κ2S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  30. The crystal structure of catena-poly[(E)-2-(((5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)imino)methyl)phenol], C12H15N3OS2Sn
  31. Crystal structure of dichlorido(N-o-tolyl-1,1-di-p-tolylphosphanamine–κ1P)-(methoxydi-p-tolylphosphane-κ1P)palladium(II), C36H39Cl2NOP2Pd
  32. The crystal structure of the triclinic polymorph of hexameric (trimethylsilyl)methyllithium, C24H66Li6Si6
  33. Crystal structure of bis(hydroxydi(pyridin-2-yl)methanolato-κ3N,N′O)cobalt(III) 7,7,8,8-tetracyanoquinodimethane, C34H22CoN8O4
  34. Synthesis and crystal structure of benzyl 5-oxo-5-phenyl-2-(quinolin-2-yl)pentanoate, C27H23NO3
  35. Crystal structure of 5,5-dimethyl-3-oxocyclohex-1-en-1-yl 4-(2,2-dichloroacetyl)-3,4-dihydro-2 H-benzo[b][1,4]oxazine-7-carboxylate, C19H19Cl2NO5
  36. Crystal structure of dipentyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C18H28O6
  37. The crystal structure of catena-poly[diaqua-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)dicadmium(II)], C30H18Cd2N2O10S2
  38. Crystal structure of 2,7-diiodo-1,3,6,8-tetramethyl-bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine, C14H14B2F4I2N4
  39. A dinuclear Eu(III) complex in the crystal structure of dodecaaqua-bis(μ2-4-(1H-tetrazol-5-yl)benzoato-κ2O:O′) bis(5-(4-carboxylatophenyl)tetrazol-1-ide) tetrahydrate, C32H50Eu2N16O24
  40. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one, C24H18F2N2O3S
  41. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-acetamidophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one-methanol-hydrate (2/1/1), C53H50F2N6O10S2
  42. Crystal structure of 4-dimethylamino-pyridin-1-ium uracil-1-acetate, C13H16N4O4
  43. Crystal structure of dimethylammonium 5-fluorouracil-1-acetate, C8H12N3O4F
  44. Crystal structure of bis(N′-((5-(ethoxycarbonyl)-1H-pyrrol-2-yl)methylene)-N-ethylcarbamohydrazonothioato-κ2N,O)nickel(II), C22H30N8O4S2Ni
  45. Crystal structure of chlorido-(η5-pentamethylcyclopentadienyl)-((bis-pyrazol-1-yl)methane-κ2N,N′) rhodium(III) hexafluorophosphate. (C17H23ClN4RhF6P)
  46. The crystal structure of 5-(benzofuran-2-carbonyl)-N-cyclohexyl-5,6-dihydrophenanthridine-6-carboxamide, C29H26N2O3
  47. The crystal structure of 2-oxo-2H-chromen-4-yl acetate, C11H8O4
  48. The crystal structure of 2-nitroisophthalic acid, C8H5NO6
  49. Crystal structure of 3-fluoro-9-methoxy-4b,5,14,15-tetrahydro-6H-isoquinolino [2′,1′:1,6]pyrazino[2,3-b]quinoxaline, C19H17FN4O
  50. Crystal structure of (4-fluorobenzyl-κC)(bis(2-hydroxyethyl) carbamodithioato-κ2S,S′)(2,2′-imino-diethanolato-κ3N,O,O′)tin(IV), C16H25FN2O4S2Sn
  51. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-bromophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18BrF3N2O3S
  52. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18ClF3N2O3S
  53. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridomanganate(II), C10H16Cl4MnN2
  54. The crystal structure of 3-carboxy-5-methylpyridin-1-ium-2-carboxylate, C8H7NO4
  55. Crystal structure of bis(3-methoxy-N-(1-(pyridin-2-yl)ethylidene)benzohydrazonato κ3O,N,N′)zinc(II), C30H28N6O4Zn
  56. Crystal structure of dichlorido-(4,4′-dichloro-2,2′-bipyridine-κ2N,N′)platinum(II) — acetone (1/1), C13H12Cl4N2PtO
  57. Crystal structure of diethyl 6,12-bis(4-fluorophenyl)-2,10-dimethoxy-3,9-diphenyl-3,9-diazatetracyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C42H42F2N2O6
  58. Synthesis and crystal structure of (1E,3E)-2-hydroxy-5-methylisophthalaldehyde O,O-di(2-((((E)-(2-hydroxynaphthalen-1-yl)methylene)amino)oxy)ethyl) dioxime, C35H32N4O7
  59. The crystal structure of 2-phenyl-4,6-bis(prop-2-yn-1-yloxy)-1,3,5-triazine, C15H11N3O2
  60. Crystal structure of 7-(2-{4-[(4-bromophenyl)methyl]piperazin-1-yl}ethoxy)-2H-chromen-2-one, C22H23BrN2O3
  61. Crystal structure of bis-[N-(3-ethyl-1-pyrazin-2-yl-ethylidene)-3-bromo-benzoic acid-hydrazonato-κ3O,N,N′)]-cadmium(II), C30H28N8O2Br2Cd
  62. Crystal structure of 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one, C12H9FO3
  63. Crystal structure of 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid, C14H18O4
  64. The crystal structure of 3-bromo-6-methoxy-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, C13H19BBrNO3
  65. The crystal structure of 6-methyl-3,20-dioxo-19-norpregna-4,6-dien-17-yl acetate–2,4-dihydroxybenzoic acid (1/1), C30H36O8
  66. The crystal structure of (5-chloro-2-hydroxy-N-(4-methoxy-2-oxidobenzylidene)benzohydrazonato-κ3N,O,O′)-(pyridine-κ1N)copper(II), C20H16ClCuN3O4
  67. Crystal structure of (E)-2-cyano-N′-(1-(3-ethylpyrazin-2-yl)ethylidene)acetohydrazide, C11H3N5O
  68. Crystal structure of (2,7-dihexyl-9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane), C51H56OP2
  69. Crystal structure of 5-((bis(pyridin-2-ylmethyl)amino)methyl)quinolin-8-ol, C22H20N4O
  70. Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
  71. The crystal structure of [(tetra-μ2-2,6-difluorobenzoato-κ2O:O′)-bis-(2,6-difluorobenzoato-κ2O:O′)-bis-(1,10-phenanthroline-κ2N:N′)]dierbium(III) C66H34N4O12F12Er2
  72. Crystal structure of bis(3-chloro-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-k3N,N′,O)nickel(II), C26H20N8O2Cl2Ni
  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
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