Home Physical Sciences The crystal structure of ethyl 2,3,5-trifluoro-4-(4-oxo-3,4-dihydropyridin-1(2H)-yl)benzoate, C14H12F3NO3
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The crystal structure of ethyl 2,3,5-trifluoro-4-(4-oxo-3,4-dihydropyridin-1(2H)-yl)benzoate, C14H12F3NO3

  • Jingjing Wang , Yundeng Wu ORCID logo EMAIL logo and Yong Li
Published/Copyright: September 9, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 6

Abstract

C14H12F3NO3, monoclinic, P21/n (no. 14), a = 14.4583(12) Å, b = 6.6553(5) Å, c = 14.8395(11) Å, β = 113.733(3)°, V = 1307.16(18) Å3, Z = 4, Rgt (F) = 0.0479, wRref (F 2) = 0.1235, T = 170 K.

CCDC no.: 2203680

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: 0.49 × 0.35 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.14 mm−1
Diffractometer, scan mode: Bruker Apex-II, φ and ω
θ max, completeness: 27.1°, >99%
N(hkl)measured, N(hkl)unique, R int: 14976, 2893, 0.034
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2371
N(param)refined: 195
Programs: Bruker [1], Shelx [2, 3], Olex2 [4]
Table 2:

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

Atom x y z U iso*/U eq
C1 0.56532(14) 0.1236(3) 0.82490(13) 0.0375(4)
H1 0.539511 0.010678 0.783091 0.045*
C2 0.56691(16) 0.1169(3) 0.91668(14) 0.0440(5)
H2 0.550094 −0.004842 0.939978 0.053*
C3 0.59367(16) 0.2911(3) 0.97965(14) 0.0449(5)
C4 0.60731(17) 0.4828(3) 0.93043(14) 0.0469(5)
H4A 0.540671 0.547446 0.895571 0.056*
H4B 0.650649 0.577144 0.981546 0.056*
C5 0.65411(15) 0.4432(3) 0.85873(13) 0.0399(4)
H5A 0.653172 0.567961 0.822004 0.048*
H5B 0.725410 0.402102 0.894832 0.048*
C6 0.59421(13) 0.2852(2) 0.69312(12) 0.0282(4)
C7 0.67659(12) 0.3364(3) 0.67109(12) 0.0303(4)
C8 0.67268(13) 0.3394(2) 0.57729(12) 0.0296(4)
H8a 0.730967 0.375863 0.566561 0.036*
C9 0.58365(13) 0.2893(2) 0.49755(12) 0.0286(4)
C10 0.50001(13) 0.2400(2) 0.51691(12) 0.0289(4)
H10b 0.437997 0.207169 0.463928 0.035*
C11 0.50581(12) 0.2381(2) 0.61215(13) 0.0289(4)
C12 0.57797(14) 0.2884(2) 0.39492(12) 0.0318(4)
C13 0.67172(17) 0.3126(3) 0.29616(13) 0.0454(5)
H13A 0.636642 0.434327 0.260246 0.054*
H13B 0.637732 0.192924 0.257314 0.054*
C14 0.78049(18) 0.3164(4) 0.31139(16) 0.0518(5)
H14A 0.785215 0.324143 0.247434 0.078*
H14B 0.813922 0.193768 0.345614 0.078*
H14C 0.813566 0.433898 0.351113 0.078*
F1 0.76544(7) 0.37929(19) 0.74621(7) 0.0409(3)
F2 0.42129(8) 0.19484(17) 0.62593(8) 0.0396(3)
F3a 0.41065(9) 0.19627(19) 0.44519(9) 0.0368(3)
F3Ab 0.7544(4) 0.3951(10) 0.5745(4) 0.0368(3)
N1 0.59892(11) 0.2844(2) 0.78928(10) 0.0316(3)
O1 0.59685(14) 0.2919(3) 1.06346(11) 0.0600(5)
O2 0.50037(11) 0.2738(2) 0.32234(9) 0.0445(4)
O3 0.66926(10) 0.3057(2) 0.39382(9) 0.0399(3)

  1. aOccupancy: 0.841(2), bOccupancy: 0.159(2).

Source of material

In a representative experiment, the title compound commercially available was grown by the vapor diffusion method. Approximately 0.14 g (0.5 mmol) ethyl 2,3,5-trifluoro-4-(4-oxo-3,4-dihydropyridin- 1(2H)-yl)benzoate was dissolved in dichloromethane/methanol (1:1) solution dropwise in a well. Then n-pentane was added into another well. Both wells were sitting in a clear beaker sealed with tape for easy viewing and access. Over time the equilibrium of the vapor will exist between the solvents. During this equilibration process colorless plate crystals of the title compound were obtained within about a week.

Experimental details

A suitable crystal was selected and placed on a ‘Bruker Apex–II CCD’ diffractometer. Using Olex2 [4], the structure was solved with the ShelXT [2] structure solution program and refined with the ShelXT [3] refinement package.

U iso values of hydrogen atoms were set to 1.2U eq of the parent atoms for all C(H) groups, C(H,H) groups, and at 1.5U eq for all C(H,H,H) groups. Secondary CH2, C5(H5A,H5B), C13(H13A,H13B), C4(H4A,H4B), were refined with riding coordinates. Aromatic/amide H, C10(H10), C8(H8), C1(H1), C2(H2), were also refined with riding coordinates. Idealised Me, C14(H14A,H14B,H14C), were refined as rotating group. Statistical disorder is noted for the F3, F3A atom. The F3, F3A are disordered over two sites with occupancies 0.8414:0.1586. For this disorder, distances restraints of F3–C10 and F3A–C8, and U iso/U aniso restraints of U anis(F3) = U anis(F3A) were imposed. The disordered F atom in 1,2,4-trifluorobenzene group is also observed in related systems [5], [6], [7], [8].

Comment

Contezolid with a strong potency against all major Gram-positive pathogens, including newer multidrug resistant strains, has gained a significant place as a last line antimicrobial agent [9, 10]. It is known that even very little structural changes to the oxazolidinone lead to drastic changes in biological activity [11, 12]. The title compound, a derivative of Contezolid, replaces its oxazolidinone group with a ethyl formate group which is expected to change conformations when they are bound to target nucleotides. The title compound is part of our continuing interest in the structure-activity relationship about the antimicrobial agent, and understanding of hydrogen bonding schemes of related compounds [13, 14].

The title compound has a trifluorinated benzyl group whose structure was determined without disorder by Refs. [15], [16], [17]. The trifluorinated benzyl group perhaps plays a part in toxicity and selective binding to bacteria according to cryo–EM results [9]. The structure of 2,3,5-trifluorobenzoic acid moiety, most similar to the title compound, has been reported by Refs. [18], [19], [20].

To the best of our knowledge, this is the first article to report a structure containing the ethyl 2,3,5-trifluorobenzoate group, and the first to report a structure containing the 2,3–dihydro-4-pyridinone group.

The asymmetric unit of the title structure contains one ethyl 2,3,5-trifluoro-4-(4-oxo-3,4-dihydropyridin-1(2H)-yl)benzoate (cf. left part of the figure, main part of the disorder is shown for clarity purpose). The bond lengths and angles within these moieties are in the expected ranges. The plane of 2,3–dihydro-4-pyridinone group (N1—C1—C2—C3—C4—C5—C6), encloses an angle of 53.87(9)° with the plane of the trifluorobenzoate group (C6—C7—C8—C9—C10—C11).

No classic hydrogen bond was found for the title compound, but two intermolecular non-classical hydrogen bonds.

Two hydrogen bonds (C4—H4A…O1′; ′ = 1−x, 1−y, 2−z; D…A = 3.344(3) Å) connect two adjacent molecules to form an eight-membered ring. The other two hydrogen bonds (C1—H1…O2″; ″ = 1−x, −y, 1−z; D…A = 3.317(2) Å) connect the next two adjacent molecules head-to-tail forming a large ring (cf. right part of the figure. Some hydrogen atoms are omitted for clarity). The two rings extend alternately, constructing chains parallel to the diagonal of the bc plane (cf. right part of the figure).

Corresponding author: Yundeng Wu, Technique Center, Jinling Pharmaceutical Company Limited, Nanjing 210046, Jiangsu Province, P. R. China, E-mail:

Funding source: School of Chemical Engineering, Ningbo Polytechnic

Funding source: Ningbo Polytechnic Zhejiang Collaborative Innovation Center

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

  2. Research funding: This work was funded by School of Chemical Engineering, Ningbo Polytechnic, and Ningbo Polytechnic Zhejiang Collaborative Innovation Center.

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

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Received: 2022-07-06
Accepted: 2021-12-02
Published Online: 2022-09-09
Published in Print: 2022-12-16

© 2022 the author(s), published by De Gruyter, Berlin/Boston

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

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  51. Crystal structure of (E)-N-(4-morpholinophenyl)-1-(quinolin-2-yl)methanimine, C20H19N3O
  52. The crystal structure of catena-poly[(1,10-phenanthroline-κ2 N,N′)-(μ3-2-hydroxybenzene-1,3-dicarboxylato-κ5 O,O′:O″,O‴:O‴)cadmium(II)], C20H12CdN2O5
  53. The crystal structure of 2,6-di-tert-butyl-4-(4-(methylthio)benzylidene)cyclohexa-2,5-dien-1-one, C22H28OS
  54. La3.65Mg30Sb1.07 as a disordered derivative of Th2Ni17-type structure
  55. Crystal structure of (E)-N-(4-morpholinophenyl)-1-(quinoxalin-2-yl)methanimine, C19H18N4O
  56. The crystal structure of 2,2′-(1,2-phenylenebis(methylene))bis(1,3-dimethylisothiouronium) bromide, C14H24Br2N4S2
  57. Crystal structure of tetraaqua-bis[4-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N]zinc(II), C18H20ZnN6O8
  58. Crystal structure of bis(tricarbonyl)-{(S)-(tert-butoxycarbonyl)(1-methoxy-1-oxo-3-sulfido-k2 S:S′-propan-2-yl)amido-k2N:N′}diiron(I) (Fe—Fe), C15H15Fe2NO10S
  59. Crystal structure of (E)-3-((4-chlorophenyl)thio)-4-hydroxypent-3-en-2-one, C11H11ClO2S
  60. The crystal structure of (E)-3′,6′-bis(diethylamino)-2-((5-(diethylamino)-2-hydroxybenzylidene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C39H45N5O3
  61. The crystal structure of 2-(4-methoxynaphthalen-1-yl)-4H-chromen-4-one, C20H14O3
  62. The crystal structure of trans-dichlorido-(ethylenediamine-κ 2 N,N′)-bis(triphenylphosphine-κ 1 P)ruthenium(II), C38H38Cl2N2P2Ru
  63. The double polymeric chain of catena-poly[(μ2-6-bromopyridine-3-carboxylato-κ2 O,O′) (6-bromopyridine-3-carboxylato-κ2 O,O′) (μ2-1,2-bis(4-pyridyl)ethylene-κ2 N:N′)cobalt(II)], C24H16CoBr2N4O4
  64. The crystal structure of tert-butyl 2-(4-(12-bromo [2.2]paracyclophanyl)carbamoyl)pyrrolidine-1-carboxylate, C26H31BrN2O3
  65. The crystal structure of (Z)-2-(2,3-dimethoxybenzylidene)naphtho[1,2-b]furan-3(2H)-one, C21H16O4
  66. Crystal structure of 2-hydroxy-1-tosylindolin-3-yl- 2-naphthoate, C26H21N1S1O5
  67. The crystal structure of 1-methyl-N-(1-methyl-1H-imidazole-2-carbonyl)-1H-imidazole-2-carboxamide, C10H11N5O2
  68. The crystal structure of (E)-2-((5-bromo-2-hydroxybenzylidene)amino)-3′,6′-bis(ethylamino)-2′, 7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one, C33H31BrN4O3
  69. The crystal structure of dimethanol-5,15-diphenylporphyrin-21,23-diido-κ4 N,Nʹ,Nʺ,Nʹʺ-manganese(III) trans-dicyanido-bis(acetylacetonato-κ2O,Oʹ)ruthenium(III), C46H42N6O6RuMn
  70. Crystal structure of 1,4,8,11-tetraazacyclotetradecane-1,8-diium bis(3,5-dicarboxybenzoate), C28H36N4O12
  71. Bifurcated halogen bonds in the crystal structure of 2,2′-bi(1,8-naphthyridine)—1,4-diiodotetrafluorobenzene (1/1), C22H10F4I2N4
https://doi.org/10.1515/ncrs-2022-0412
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 1,5-bis(4-chlorophenyl)-3-(3-methylphenyl)pentane- 1,5-dione, C48H40Cl4O4
  4. Crystal structure of (bis(1,10-phenanthroline-κ 2 N,N′))-(3,5-dinitrosalicylato-κ 2 O,O′)nickel(II), C31H18N6NiO7
  5. Crystal structure of {N,N′-bis(4-fluoro-salicylaldehyde)-3,6-dioxa-1,8-diaminooctane-κ4 O,N,N′,O′}zinc(II), C20H20F2N2O4Zn
  6. [5-Bromo-2-(2-(dimethylamino)ethyliminomethyl)phenolato-κ3 N,N′,O]-isothiocyanato-nickel(II), C12H14BrN3NiOS
  7. Crystal structure of 9-bromo-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin- 2-amine, C18H15BrN4O
  8. The crystal structure of imidazolium nitrate, C3H5O3N3
  9. Crystal structure of diiodido-bis(6,6′-dimethoxy-2,2′-(ethane-1,2-diylbis(nitrilomethanylylidene)) diphenolato)tricadmium(II), C36H36Cd3I2N4O8
  10. Crystal structure of [diaqua-bis(2-((1H-tetrazol-1-yl)methyl)-5-carboxy-1H-imidazole-4-carboxylato-κ2 N,O) manganese(II)] dihydrate, C14H18MnN12O12
  11. Crystal structure of Diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-k4 O,O′,N,N′)]iron(II), C13H14FeN4O10
  12. Crystal structure of poly[dimethanol-κ1O-(µ2-(E)-2-((2-oxidobenzylidene)amino)acetato)-(µ3-(E)-2-((2-oxidobenzylidene)amino)acetato)dicadmium(II)], C20H22Cd2N2O8
  13. Crystal structure of N 2,N 6-bis(2-(((E)-quinolin-8-ylmethylene)amino)phenyl)pyridine-2,6-dicarboxamide, C39H27N7O2
  14. An I 6 2 − anion in the crystal structure of theophyllinium triiodide monohydrate, C7H11I3N4O3
  15. The crystal structure of poly[6,6′-oxybis(4-(pyridin-1-ium-1-yl)-1,3,5,2,4,6-trioxatriborinan-2-olate)], [B6O9](C5H5N)2
  16. The crystal structure of (carbonato κ2 O,O′)(2-oxopyridin-1(2H)-olato-κN)tris(trimethylphosphine)rhodium(III) water solvate, C15H33NO5P3Rh
  17. The crystal structure of dibromido-bis((RS)-2-(4-chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile-κ1 N)zinc(II), C30H34Br2Cl2N8Zn
  18. Synthesis and crystal structure of 3-(((7-hydroxy-3-(4-hydroxy-3,5-dinitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)(nitroso)amino)propanoic acid, C19H14N4O11
  19. The crystal structure of 3-((4-chloro-N-(2-methoxyethyl)benzamido)methyl)phenyl methanesulfonate, C18H20ClNO5S
  20. Crystal structure of di([1,1′:3′,1″-terphenyl]-2′-yl)tellane, C36H26Te
  21. The crystal structure of diaqua-bis(pyrazolo[1,5-a]-pyrimidine-3-carboxylato-κ2 N,O)zinc(II), C14H12N6O6Zn
  22. Crystal structure of N′,N‴-((1E,2E)-1,2-diphenylethane-1,2-diylidene)bis(4-methylbenzohydrazide) – water – methanol (1/1/1), C31H32N4O4
  23. Crystal structure of 3-((2,4-dichlorobenzyl)thio)-5-methyl-7-(trifluoromethyl)-[1,2,4]triazolo [4,3-c]pyrimidine, C14H9Cl2F3N4S
  24. Crystal structure of 3,5,6,7-tetramethoxy-3′,4′-methylenedioxy-flavone, C20H18O8
  25. Crystal structure of catena-poly[(5,5′-dimethyl-2,2′-bipyridine-κ 2 N,N′)-(μ 3-hydrogen-1,1′,1″-(1,3,5-triazine-2,4,6-triyl)tris(piperidine-4-carboxylato)- κ 5 O:O,O′:O″,O‴)-cadmium(II)], C33H40CdN8O6
  26. The crystal structure of 3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C9H17N3
  27. Crystal structure of [(1,4,7,10-tetraoxacyclododecane-κ 4 O,O′,O″, O‴)-tris(nitrato-κ 2 O,O′)gadolinium(III)], C8H16N3O13Gd
  28. The crystal structure of 2,2′-((pyridine-2,6-diylbis(methylene))bis(sulfanediyl))-bis(4,5-dihydro-1H-imidazol-3-ium) bromide, C13H19Br2N5S2
  29. Crystal structure of E-2-chloro-N′-(1-(5-chloro-2-hydroxyphenyl)propylidene)benzohydrazide, C16H14Cl2N2O2
  30. Crystal structure of 3-(adamantan-1-yl)-4-methyl-5-{[(4-nitrophenyl)methyl]sulfanyl}-4H-1,2,4-triazole, C20H24N4O2S
  31. The crystal structure of dimethanol-κ1O-(5,10,15,20-tetrakis(4-nitrophenyl)porphyrin-21,23-diido-κ4 O,O′,O″,O′″)manganese(III) trans-dicyanido-κ1C-bis(acetylacetonato-κ2 O,O′)ruthenium(III), C58H46N10O14RuMn
  32. The crystal structure of nitroxyl-κ N-{hydridotris(3-trifluoromethyl-5-methylpyrazolyl-1-yl-κN 3)borato}nickel(II), C15H13BF9N7NiO
  33. The crystal structure of [(2,2′-bipyridine-κ2 N,N)-bis(6-phenylpyridine-2-carboxylato- κ2 N,O)nickel(II)] monohydrate, C34H26N4O5Ni
  34. The crystal structure of 5-(2-fluoro-3-methoxyphenyl)-1-(2-fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione, C20H15F5N2O3
  35. The crystal structure of ethyl 2,3,5-trifluoro-4-(4-oxo-3,4-dihydropyridin-1(2H)-yl)benzoate, C14H12F3NO3
  36. [2,2′-{Ethane-1,2-diylbis[(azanylylidene)methanylylidene]}bis(3-bromo-2-hydroxyphenyl)]iron(III) nitrate, C20H12Br2CuN2O2
  37. The crystal structure of 1-(2-iodophenyl)-4-phenyl-1H-1,2,3-triazole, C14H10IN3
  38. Synthesis and crystal structure of 2-(2-oxo-2-(thiophen-2-yl)ethyl)-4H-chromen-4-one, C15H10O3S
  39. {6,6′-((1E,1′E)-((2,2-dimethylpropane-1,3-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(2-bromo-4-chlorophenolate)-κ4N,N′,O,O′}copper(II), C19H16Br2Cl2CuN2O2
  40. The crystal structure of N′-[bis(2-hydroxyphenyl)methylidene]pyridine-4-carbohydrazide, C19H15N3O3
  41. Crystal structure of 2-chloro-6-formylphenolato-κ2O,O′-(6,6′-(((2,2-dimethylpropane-1,3-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(2-chlorophenolato)κ4 N,N,O,O′)cobalt(III), C26H22Cl3CoN2O4
  42. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylate-κ 2 N,O)-bis(μ2-6-phenylpyridine-2-carboxylate-κ 2 O:O′)-bis(μ2-6-phenylpyridine-2-carboxylate-κ 3N,O:O)tetralead(II) C48H32N4O8Pb2
  43. The crystal structure of 3,7-dihydroxy-9-methoxy-4a-methyl-4aH-benzo[c] chromene-2,6-dione —dichloromethane (1/1), C16H14Cl2O6
  44. The crystal structure of (Z)-6-(((5-chloro-2-hydroxyphenyl)amino)methylene)- 4-nitrocyclohexa, C13H9ClN2O4
  45. Crystal structure of dichlorido-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1 N)zinc(II), C60H68O4N12Cl10Zn
  46. The crystal structure of 4-(2-bromoethoxy)-2-hydroxybenzaldehyde, C9H9BrO3
  47. The crystal structure of 5-azido-1-methyl-4-nitroimidazole, C4H4O2N6
  48. Crystal structure of dibromido-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II), C60H68O4N12Br2Cl8Zn
  49. Crystal structure of tetrasodium-bis(μ 2-oxido)-hexafluoro-didioxo-molybdenum(V), Na2(Mo2O4F6)
  50. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-4- hydroxybenzohydrazide-water (1/1), C14H13Cl1N2O4
  51. Crystal structure of (E)-N-(4-morpholinophenyl)-1-(quinolin-2-yl)methanimine, C20H19N3O
  52. The crystal structure of catena-poly[(1,10-phenanthroline-κ2 N,N′)-(μ3-2-hydroxybenzene-1,3-dicarboxylato-κ5 O,O′:O″,O‴:O‴)cadmium(II)], C20H12CdN2O5
  53. The crystal structure of 2,6-di-tert-butyl-4-(4-(methylthio)benzylidene)cyclohexa-2,5-dien-1-one, C22H28OS
  54. La3.65Mg30Sb1.07 as a disordered derivative of Th2Ni17-type structure
  55. Crystal structure of (E)-N-(4-morpholinophenyl)-1-(quinoxalin-2-yl)methanimine, C19H18N4O
  56. The crystal structure of 2,2′-(1,2-phenylenebis(methylene))bis(1,3-dimethylisothiouronium) bromide, C14H24Br2N4S2
  57. Crystal structure of tetraaqua-bis[4-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N]zinc(II), C18H20ZnN6O8
  58. Crystal structure of bis(tricarbonyl)-{(S)-(tert-butoxycarbonyl)(1-methoxy-1-oxo-3-sulfido-k2 S:S′-propan-2-yl)amido-k2N:N′}diiron(I) (Fe—Fe), C15H15Fe2NO10S
  59. Crystal structure of (E)-3-((4-chlorophenyl)thio)-4-hydroxypent-3-en-2-one, C11H11ClO2S
  60. The crystal structure of (E)-3′,6′-bis(diethylamino)-2-((5-(diethylamino)-2-hydroxybenzylidene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C39H45N5O3
  61. The crystal structure of 2-(4-methoxynaphthalen-1-yl)-4H-chromen-4-one, C20H14O3
  62. The crystal structure of trans-dichlorido-(ethylenediamine-κ 2 N,N′)-bis(triphenylphosphine-κ 1 P)ruthenium(II), C38H38Cl2N2P2Ru
  63. The double polymeric chain of catena-poly[(μ2-6-bromopyridine-3-carboxylato-κ2 O,O′) (6-bromopyridine-3-carboxylato-κ2 O,O′) (μ2-1,2-bis(4-pyridyl)ethylene-κ2 N:N′)cobalt(II)], C24H16CoBr2N4O4
  64. The crystal structure of tert-butyl 2-(4-(12-bromo [2.2]paracyclophanyl)carbamoyl)pyrrolidine-1-carboxylate, C26H31BrN2O3
  65. The crystal structure of (Z)-2-(2,3-dimethoxybenzylidene)naphtho[1,2-b]furan-3(2H)-one, C21H16O4
  66. Crystal structure of 2-hydroxy-1-tosylindolin-3-yl- 2-naphthoate, C26H21N1S1O5
  67. The crystal structure of 1-methyl-N-(1-methyl-1H-imidazole-2-carbonyl)-1H-imidazole-2-carboxamide, C10H11N5O2
  68. The crystal structure of (E)-2-((5-bromo-2-hydroxybenzylidene)amino)-3′,6′-bis(ethylamino)-2′, 7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one, C33H31BrN4O3
  69. The crystal structure of dimethanol-5,15-diphenylporphyrin-21,23-diido-κ4 N,Nʹ,Nʺ,Nʹʺ-manganese(III) trans-dicyanido-bis(acetylacetonato-κ2O,Oʹ)ruthenium(III), C46H42N6O6RuMn
  70. Crystal structure of 1,4,8,11-tetraazacyclotetradecane-1,8-diium bis(3,5-dicarboxybenzoate), C28H36N4O12
  71. Bifurcated halogen bonds in the crystal structure of 2,2′-bi(1,8-naphthyridine)—1,4-diiodotetrafluorobenzene (1/1), C22H10F4I2N4
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