Startseite Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2
Artikel Open Access

Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2

  • Xiaoru Pan ORCID logo EMAIL logo und Xiang-Yan Kong
Veröffentlicht/Copyright: 14. November 2024

Abstract

C7H3ClF3NO2, triclinic, P 1 (no. 2), a = 5.8837(5) Å, b = 14.1634(14) Å, c = 15.3120(15) Å, α = 92.667(5)°, β = 100.364(5)°, γ = 99.475(5)°, V = 1,234.2(2) Å3, Z = 6, R gt(F) = 0.0458, wR ref(F 2) = 0.1012, T = 298 K.

CCDC no.: 2390150

A part of 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 block
Size: 0.25 × 0.22 × 0.19 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.49 mm−1
Diffractometer, scan mode: φ and ω
θ max, completeness: 25.4°, 99 %
N(hkl)measured , N(hkl)unique, R int: 23,454, 4,471, 0.070
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2,937
N(param)refined: 382
Programs: Bruker, 1 Olex2, 2 Shelx 3 , 4
Table 2:

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

Atom x y z U iso*/U eq
C1 0.2636 (6) 0.4687 (3) 0.6837 (2) 0.0365 (8)
C2 0.8368 (6) 0.1578 (2) 0.6904 (2) 0.0373 (8)
C3 0.9119 (6) 0.0732 (2) 0.6699 (2) 0.0385 (8)
C4 1.1063 (6) 0.0491 (2) 0.7237 (2) 0.0401 (8)
H4A 1.156252 −0.008325 0.711773 0.048*
C5 1.2247 (6) 0.1117 (2) 0.7956 (2) 0.0399 (8)
C6 1.1453 (6) 0.1965 (2) 0.8104 (2) 0.0406 (8)
H6 1.226882 0.239396 0.857844 0.049*
C7 1.4285 (7) 0.0856 (3) 0.8565 (3) 0.0502 (10)
C8 0.6196 (6) 0.1883 (2) 0.6393 (2) 0.0386 (8)
C9 0.1033 (6) 0.4014 (2) 0.6102 (2) 0.0351 (8)
C10 −0.1115 (5) 0.4193 (2) 0.5669 (2) 0.0330 (8)
C11 −0.2349 (6) 0.3596 (2) 0.4933 (2) 0.0372 (8)
H11 −0.379362 0.370605 0.463570 0.045*
C12 −0.1396 (6) 0.2839 (2) 0.4653 (2) 0.0391 (8)
C13 0.0724 (6) 0.2683 (2) 0.5136 (2) 0.0386 (8)
H13 0.134858 0.216116 0.495539 0.046*
C14 −0.2575 (7) 0.2212 (3) 0.3826 (3) 0.0484 (10)
C15 1.0043 (6) 0.4462 (2) 0.8663 (2) 0.0356 (8)
C16 0.9620 (5) 0.5482 (2) 0.8747 (2) 0.0339 (8)
C17 1.1228 (6) 0.6228 (2) 0.9248 (2) 0.0362 (8)
C18 1.0706 (6) 0.7144 (3) 0.9249 (2) 0.0406 (8)
H18 1.177054 0.765439 0.957101 0.049*
C19 0.8602 (6) 0.7296 (2) 0.8772 (2) 0.0404 (8)
C20 0.7060 (6) 0.6516 (2) 0.8309 (2) 0.0402 (8)
H20 0.561746 0.661227 0.799770 0.048*
C21 0.7969 (7) 0.8275 (3) 0.8755 (3) 0.0505 (10)
Cl1 0.76892 (17) −0.00676 (7) 0.58095 (7) 0.0544 (3)
Cl2 −0.23564 (15) 0.51333 (6) 0.60179 (6) 0.0408 (2)
Cl3 1.38506 (15) 0.60654 (6) 0.98768 (6) 0.0443 (2)
F1 1.5735 (5) 0.1618 (2) 0.8981 (2) 0.1038 (11)
F2 1.3637 (5) 0.0293 (3) 0.91657 (19) 0.1004 (11)
F3 1.5587 (4) 0.03892 (18) 0.81383 (16) 0.0657 (7)
F4 −0.2537 (4) 0.12856 (15) 0.39419 (15) 0.0596 (6)
F5 −0.1496 (4) 0.24165 (18) 0.31420 (15) 0.0675 (7)
F6 −0.4806 (4) 0.23026 (16) 0.35713 (15) 0.0631 (7)
F7 0.8980 (5) 0.88286 (18) 0.94834 (18) 0.0886 (9)
F8 0.5677 (4) 0.82491 (16) 0.86657 (19) 0.0753 (8)
F9 0.8588 (5) 0.87280 (17) 0.80740 (19) 0.0813 (8)
N1 0.9575 (5) 0.21897 (19) 0.75968 (18) 0.0376 (7)
N2 0.1898 (5) 0.3246 (2) 0.58444 (19) 0.0383 (7)
N3 0.7554 (5) 0.5630 (2) 0.82903 (18) 0.0366 (7)
O1 0.5135 (5) 0.1527 (2) 0.56895 (19) 0.0727 (9)
O2 0.5640 (4) 0.25987 (19) 0.68238 (18) 0.0547 (7)
H2 0.452276 0.278000 0.651887 0.082*
O3 0.2722 (4) 0.55476 (18) 0.68516 (16) 0.0460 (6)
O4 0.3963 (4) 0.42388 (17) 0.73961 (15) 0.0408 (6)
H4 0.506791 0.462684 0.768042 0.061*
O5 0.8787 (4) 0.40116 (16) 0.79141 (15) 0.0422 (6)
H5 0.899320 0.345340 0.788287 0.063*
O6 1.1332 (4) 0.41117 (17) 0.92094 (15) 0.0436 (6)

1 Source of materials

3-Chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid (HL) and tetrahydrofuran (THF) were purchased from Thermo Fisher Scientific Inc. Deionized water is prepared by the purification equipment purchased by our college. The preparation of the crystal structure for the title compound is very simple. 0.5 g (2.217 mmol) of HL was added to a 10 mL glass tube with a mixed solution of THF and deionized water (6 mL, 3:3, v/v). Subsequently, the glass tube is positioned in a dark area with adequate ventilation. The slow evaporation of the solution yielded colourless block-shaped crystals within 1 week, yielding 43 % (based on the HL organic ligand).

2 Experimental details

The crystal structure of the complex was solved using the Shelxt program with intrinsic phasing method and refined by the full-matrix least-squares method with the Shelxl program. All non-hydrogen atoms (Ca–, C–, N– and O–atom) were refined with anisotropic displacement parameters, while the hydrogen atoms were placed in idealized positions with isotropic thermal parameters.

3 Comment

As a molecular building block, 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid (HL) features a distinctive combination of a chlorine atom and a trifluoromethyl group attached to a pyridinecarboxylic ring, which endows it with unique electronic properties and potential applications in the medical field. 5 , 6 , 7 , 8 However, the crystal structure of HL has not been exploited. Hence, to better understand the nature of HL, the title structure was synthesized. HL crystallizes in the triclinic system with P 1 space group. The asymmetric unit contains three crystallographically independent HL organic ligands. The bond lengths other than those of C–C bonds, i.e., the C–N, C–O, C–Cl and C–F distances are of 1.326(4)–1.350(4) Å, 1.187(4)–1.311(4) Å, 1.722(3)–1.728(3) Å and 1.312(5)–1.338(4) Å. The bond lengths observed in this study are within the normal range, comparable to those reported in crystal structures containing similar atoms. 9 , 10 , 11 , 12 Notably, the hydrogen atoms on the carboxyl groups of the HL ligands remain intact. For this reason, the three originally independent HL ligands formed a non-covalently bonded cyclic structure through the intermolecular interaction of O–H⋯N hydrogen bonding (O2–H2⋯N2, O4–H4⋯N3 and O5–H5⋯N1; distance range between donor and acceptor atoms: 2.7329(3)–2.7492(3) Å and finally resulted in a 3D extended network with the help of other short contacts (O–H⋯O, C–H⋯O and C–H⋯F).


Corresponding author: Xiaoru Pan, College of Chemistry and Chemical Engineering, Weifang University, Weifang, Shandong 261061, P.R. China, E-mail:

Funding source: Weifang Science and Technology Development Plan Project

Award Identifier / Grant number: 2019GX007

Acknowledgments

Special thanks are given to Xiang-Yan Kong for his valuable suggestions on the writing logic and content of the manuscript.

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

  2. Research funding: Weifang Science and Technology Development Plan Project (No. 2019GX007).

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

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Received: 2024-10-10
Accepted: 2024-11-04
Published Online: 2024-11-14
Published in Print: 2025-02-25

© 2024 the author(s), published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
  4. Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
  5. Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
  6. Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
  7. Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
  8. Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
  9. The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
  10. The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
  11. The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
  12. The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
  13. Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  14. The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
  15. The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
  16. Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
  17. The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
  18. Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
  19. The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
  20. The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
  21. Crystal structure of (−)-flavesine H, C15H22N2O2
  22. Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
  23. Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
  24. The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
  25. The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
  26. Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
  27. The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
  28. The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
  29. The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
  30. Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
  31. Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
  32. Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
  33. Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
  34. Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
  35. Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
  36. The crystal structure of 1,1,1,2,2,2-hexakis(2-methyl-2-phenylpropyl)distannane,C60H78Sn2
  37. The crystal structure of (2,7-dimethoxynaphthalene-1,8-diyl)bis((3-nitrophenyl)methanone), C26H18N2O8
  38. Crystal structure of diaqua-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) dinitrate dihydrate, C60H76Cl8N14O14Zn
  39. The crystal structure of diphenyl bis(2-((diphenoxyphosphoryl)amino)ethyl)phosphoramidate monohydrate C40H42N3O10P3
  40. Crystal structure of 4,4′-bis(dibromomethyl)-1,1′-biphenyl, C14H10Br4
  41. Crystal structure of CaPtZn
  42. Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2
  43. The crystal structure of (3′-(2-bromophenyl)-2-phenyl-[2,2′-bioxiran]-3-yl)(phenyl)methanone, C92H68O12Br4
  44. Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2
  45. The crystal structure of bis(selenocyanato-κ1 N)-bis(methanol)-bis((1E,2E)-1,2-bis (1-(pyridin-4-yl)ethylidene)-hydrazine)iron(II) methanol solvate, C34H44FeN10O4Se2
  46. Crystal structure of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(5-(4-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one, C26H21BrN2O4
  47. The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S
  48. Crystal structure of 1′,3′-dihydro-2,2′-spirobi[indene]-1,3-dione, C17H12O2
  49. Crystal structure of (E)-2,2′,3,3′-tetrahydro-[1,1′-biindenylidene]-4,4′-diol, C18H16O2
  50. Crystal structure of di-glycylglycinium squarate dihydrate, C12H22N4O12, at 105 K
  51. Crystal structure of {[(4-fluorophenyl)methyl]triphenylphosphonium}dibromocopper(I), [C25H21FP]+[CuBr2]
  52. Crystal structure of poly[diaqua-bis(μ2-5-((pyridin-4-yl-methyl)amino)benzene-1,3-dicarboxylato-κ 2 N:O)cadmium(II)], C28H26CdN4O10
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