Startseite The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
Artikel Open Access

The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS

  • Jing Zhang ORCID logo und Lixin Zhang EMAIL logo
Veröffentlicht/Copyright: 1. März 2023

Abstract

C17H13F4NOS, triclinic, P 1 (no. 2), a = 6.1249(7) Å, b = 9.9306(10) Å, c = 13.1754(13) Å, α = 83.116(8)°, β = 80.305(9)°, γ = 73.204(9)°, V = 754.08 Å3, Z = 2, R gt (F) = 0.0460, wR ref (F 2) = 0.1078, T = 150 K.

CCDC no: 2234414

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 needle
Size: 0.14 × 0.11 × 0.08 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.26 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 25.0°, >99%
N(hkl)measured, N(hkl)unique, R int: 4888, 2652, 0.031
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2036
N(param)refined: 218
Programs: CrysAlisPRO [1], Olex2 [2], SHELX [3]
Table 2:

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

Atom x y z U iso*/U eq
S1 0.18420 (12) 0.45943 (8) 0.88482 (6) 0.0299 (2)
F1 1.0196 (3) 0.50923 (15) 0.60674 (12) 0.0295 (4)
F2 0.1815 (3) 0.18028 (19) 1.02542 (13) 0.0454 (5)
F3 0.1931 (4) 0.05626 (19) 0.90021 (15) 0.0564 (6)
F4 0.4719 (3) 0.14536 (17) 0.90564 (13) 0.0410 (4)
O1 1.2038 (3) 0.21223 (18) 0.61478 (13) 0.0235 (4)
N1 0.8326 (3) 0.2969 (2) 0.57365 (15) 0.0181 (5)
C1 0.8841 (4) 0.1918 (2) 0.42068 (19) 0.0184 (6)
C2 0.8680 (5) 0.1430 (3) 0.3288 (2) 0.0236 (6)
H2 0.728041 0.165367 0.303476 0.028*
C3 1.0672 (5) 0.0595 (3) 0.2756 (2) 0.0259 (6)
H3 1.059601 0.024370 0.214316 0.031*
C4 1.2765 (5) 0.0280 (3) 0.3122 (2) 0.0256 (6)
H4 1.408173 −0.026069 0.274375 0.031*
C5 1.2925 (4) 0.0757 (3) 0.4041 (2) 0.0228 (6)
H5 1.432562 0.053408 0.429404 0.027*
C6 1.0931 (4) 0.1579 (2) 0.45783 (19) 0.0174 (6)
C7 1.0608 (4) 0.2224 (2) 0.55712 (19) 0.0189 (6)
C8 0.7021 (4) 0.2852 (3) 0.49284 (19) 0.0202 (6)
H8A 0.637340 0.376686 0.458536 0.024*
H8B 0.579140 0.242068 0.520800 0.024*
C9 0.7342 (4) 0.3878 (2) 0.65465 (19) 0.0182 (6)
C10 0.5348 (4) 0.3750 (3) 0.71954 (19) 0.0209 (6)
H10 0.467375 0.305299 0.710621 0.025*
C11 0.4366 (4) 0.4661 (3) 0.7973 (2) 0.0225 (6)
C12 0.5317 (5) 0.5750 (3) 0.8103 (2) 0.0233 (6)
C13 0.7278 (5) 0.5868 (3) 0.7444 (2) 0.0240 (6)
H13 0.793895 0.658067 0.751200 0.029*
C14 0.8259 (4) 0.4944 (3) 0.6691 (2) 0.0216 (6)
C15 0.4248 (5) 0.6771 (3) 0.8931 (2) 0.0316 (7)
H15A 0.265369 0.719900 0.886532 0.047*
H15B 0.504101 0.748972 0.885453 0.047*
H15C 0.437121 0.627302 0.959923 0.047*
C16 0.1204 (5) 0.3001 (3) 0.8621 (2) 0.0306 (7)
H16A −0.044331 0.312885 0.878949 0.037*
H16B 0.162634 0.284809 0.789203 0.037*
C17 0.2417 (5) 0.1721 (3) 0.9229 (2) 0.0364 (8)

1 Source of materials

The 2-(chloromethyl)-N-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)benzamide (CTPB) was synthesized according to the literature method [4]. Sodium hydride (60% in oil, 0.15 g, 3.75 mmol) was washed with hexane three times and the washed sodium hydride was added to a stirred solution of CTPB (1.00 g, 2.56 mmol) in dry tetrahydrofuran (20 mL) at room temperature. The reaction mixture was continuously stirred at room temperature for 6 h and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was poured into 0.1 N hydrochloric acid, which was then brought to basic using aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was collected, and distilled under reduced pressure. The remaining substance was purified by flash column chromatography using petroleum ether: ethyl acetate (20:1, v/v) to give a white solid (0.69 g, 75.9% yield), M.p.: 85.1–86.5 °C. 5.80 mg of white solid was taken and dissolved in 10 mL of dichloromethane and 5 mL of ethanol was added. After slow volatilization for three days, crystals of the title compound were obtained.

2 Experimental details

The hydrogen atom positions were fixed geometrically at the calculated distances and allowed to ride on the parent atoms. The U iso of the H-atoms were set to 1.2 and 1.5 times U eq of the parent atoms with C–H = 0.93 Å (aromatic) and C–H = 0.97 Å (aliphatic).

3 Comment

Isoindolin-1-ones can be found in various natural and synthetic products that show a wide range of biological activities [5], [6], [7], [8], [9], [10]. Many references showed crystal structures of the derivatives with the isoindolin-1-one group [11], [12], [13], [14], [15], [16], [17], [18], [19], [20].

As shown in the figure, in the main moiety of title compound, the nitrogen atom on isoindole-1-one connects a phenyl group, and the dihedral angle between isoindole-1-one plane and phenyl plane (C9 → C14) is 55.04°. All C–C bond lengths in aromatic rings range from 1.373 to 1.407 Å. All of C–C single bond lengths are between 1.484 and 1.513 Å. N–C bonds are 1.374 and 1.468 Å. The C–S bonds are 1.779 and 1.804 Å. All bond lengths and angles are within a reasonable range [11], [12], [13], [14], [15], [16], [17], [18]. In the crystal, title molecules are linked by hydrogen bonds, which are the major intermolecular force to maintain the stability of the crystal structure. The angle of hydrogen bond C(8)–H(8B)⋯O(1) is 160°, and the length is 2.50 Å. The angle of hydrogen bond C(16)–H(16B)⋯O(1) is 163°, and the length is 2.44 Å.


Corresponding author: Lixin Zhang, College of Chemical Engineering, University of Science and Technology Liaoning, Anshan, 114051, Liaoning Province, P. R. China; and Institute of Functional Molecules, Shenyang University of Chemical Technology, Shenyang, 110142, Liaoning Province, P. R. China, E-mail:

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

  2. Research funding: None declared.

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

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Received: 2023-01-27
Accepted: 2023-02-10
Published Online: 2023-03-01
Published in Print: 2023-06-27

© 2023 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 phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
  6. The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea, C14H11Cl3N2O
  7. Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
  8. Tetrabutylammonium 1,3,5-thiadiazole-5-amido-2-carbamate—1,2,4-thiadiazole-3,5-diamine— water (1/1/1), C21H45N9O3S2
  9. The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
  10. The crystal structure of aqua-bis{2-bromo-6-((2-(2-phenylacetyl)hydrazineylidene)methyl)phenolato-κ3 N,O,O′}-dimethylformamide-κ1 O-erbium(III) chloride – dimethylformamide – water (1/2/1), C39H49N7O9Br2ClEr
  11. Crystal structure of (diaqua-bis(phenanthroline-K 2 N,N′)-tetrakis(m 2-3,4,5,6-tetrafluorophthalato-K 4 O,O:O′:O″;K 2 O:O′)dierbium (III) phenanthroline (1/2), C80H38Er2F16N8O18
  12. Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3
  13. The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3
  14. The crystal structure of catena–poly[aqua(1-naphthoato-κ 2 O,O′)-(μ-1-naphthoato-κ 4 O:O,O′:O′)lead(II)], C22H16O5Pb
  15. The crystal structure of 1-(4-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  16. The crystal structure of 4-(pyren-1-yl)butyl-4-nitrobenzoate, C27H21NO4
  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
  18. The crystal structure of catena-[nitrato-κ 2 O,O′-(μ 3-3-iodobenzene-1,2-dicarboxylato-κ 4 O:O′:O″,O‴)-(2,2′:6′,2″-terpyridine-κ 3 N,N′,N″)lanthanum(III)], C23H14IN4O7La
  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,,]chloridopalladium(II) chloride monohydrate
  20. Crystal structure of catena-poly[triaqua-[bis(m2-4-(1H-1,2,4-triazol-1-yl)benzoato-k2O:O')-(4-(1H-1,2,4-triazol-1-yl)benzoato-k1O)-praseodymium (III) monohydrate], C27H26N9O10Pr
  21. Crystal structure of trans-diaqua-bis(methyl methylcarbamohydrazonothioato-κ2 N,N′) nickel(II) iodide semihydrate, C6H22N6O2NiS2I2·0.5H2O
  22. The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
  23. The crystal structure of di-μ-1-naphthylacetato-κ 3 O,O′:O;κ 3 O:O,O′-bis[(1-naphthylacetato-κ 2 O,O′)(2,2′-bipyridine-κ 2 N,N′)lead(II)] monohydrate, C68H54N4O9Pb2
  24. Crystal structure of tetrapropylammonium guanidinium 4,4′-sulfonyldibenzoate monohydrate, C27H44N4O7S
  25. Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S
  26. Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2
  27. The crystal structure of poly[diaqua-bis(μ 3-5-bromobenzene-1,3-dicarboxylato-κ 3 O,O,O′)-(μ 2-1,3-bis-(4-pyridyl)-propane-κ 2 N,N′)-dizinc(II))] – 5-bromobenzene-1,3-dicarboxylic acid [2/1], C37H29Br3N2O14Zn2
  28. The crystal structure of 2-bromo-1,3-phenylene bis(4-methylbenzenesulfonate), C20H17BrO6S2
  29. Crystal structure of europium dichromium icosaaluminum, EuCr2Al20
  30. The crystal structure of N1,N3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4
  31. Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
  33. The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
  34. Crystal structure of E-7-fluoro-2-(2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H12F4O
  35. Crystal structure of bis(6-aminopyridine-2-carboxylato–k2O,N)-bis(N,N-dimethylformamide-k1 O)zinc(II), C18H24N6O6Zn
  36. Crystal structure of 5-(adamantan-1-yl)-3-[(4-{[2-(trifluoromethyl)phenyl]-methyl}piperazin-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione, C25H31F3N4OS
  37. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea – water (2/2/1), C30H72N10O7S2
  38. Crystal structure of tris(2,2′-bipyridine-κ2 N,N′)iron(II) triiodide – dichloromethane (2/1), C61H50Cl2Fe2I12N12
  39. Crystal structure of 2-amino-3-[2-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylideneamino]-but-2-enedinitrile, C17H17N5
  40. The crystal structure of 1-(2-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  41. Crystal structure of potassium bis(pentaselenido-κ 2 Se 1,Se 5)palladate(II), K2[Pd(Se5)2]
  42. The crystal structure of 5,10-bis(2-methoxyethyl)-5,10-dihydro-[1,2,3,4]tetrathiocino[5,6-b:8, 7-b′]diindole, C22H22N2O2S4
  43. The crystal structure of 4-(4-iodophenyl)-5H-1,2,3-dithiazole-5-thione, C8H4INS3
  44. Crystal structure of bis{μ2-(4-acetyl-phenoxy)acetato-κ2 O:O′}-bis{μ2-(4-acetyl-phenoxy)acetato-κ3 O,O′:O)- bis{(4-acetyl-phenoxy)acetato-κ2 O,O′}-bis(phenanthrolin-κ2 N,N′)didysprosium(III) tetrahydrate, C84H78N4O28Dy2
  45. Crystal structure of Eu2Pd3.37(1)Zn13.63(1)
  46. Crystal structure of 2-methoxy-4-(methoxy-carbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO5
  47. Crystal structure of catena-poly[bis(μ2-dicyanamide-κ2 N:N′)-bis(4-vinylpyridine-κN)-copper(II)], C18H14CuN8
  48. The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
  49. Synthesis and crystal structure of 1-((3R,10S,13S,17S)-10,13-dimethyl-3-(m-tolylamino)hexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO
  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
  51. The crystal structure of tetra(1-ethylimidazole-κ 1 N)-[μ 4-imidazole-4,5-dicarboxylato-κ 4 O, N, O′, N′]-trioxido-divanadium, C25H33N10O7V2
  52. The crystal structure of (E)-N′-(1-(4-fluorophenyl)propylidene)-2-hydroxybenzohydrazide, C16H15FN2O2
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