Home The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
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The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2

  • Jie Chen , Hengmei Zhu , Zhigang Cai , Jing Hu , Lili Shen , Yali Zhang and Xiaoping Xu ORCID logo EMAIL logo
Published/Copyright: February 15, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 2

Abstract

C17H8Cl2N2O2, triclinic, P 1 ‾ (no. 2), a = 7.9032(2) Å, b = 9.0843(3) Å, c = 10.8051(2) Å, α = 85.2310(10)°, β = 85.0270(10)°, γ = 71.013(2)°, V = 729.54(3) Å3, Z = 2, Rgt (F) = 0.0417, wRref (F2) = 0.1051, T = 293(2) K.

CCDC no.: 2142300

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: 0.22 × 0.13 × 0.11 mm
Wavelength: CuKα radiation (1.54184 Å)
μ: 4.10 mm−1
Diffractometer, scan mode: SuperNova, ω
θmax, completeness: 66.6°, >99%
N(hkl)measured, N(hkl)unique, Rint: 4172, 2584, 0.015
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2489
N(param)refined: 208
Programs: SuperNova [1], Olex2 [2], SHELX [3, 4]
Table 2:

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

Atom x y z Uiso*/Ueq
Cl1 0.06929 (5) 1.20154 (5) 0.46903 (4) 0.04028 (16)
Cl2 0.16636 (7) 0.99251 (6) 0.71499 (4) 0.04909 (17)
O1 0.73179 (16) 0.49158 (14) 0.50049 (11) 0.0389 (3)
O2 0.58952 (18) 0.79890 (16) 0.14137 (11) 0.0444 (3)
N1 0.69874 (18) 0.61806 (16) 0.30415 (12) 0.0309 (3)
N2 0.66662 (19) 0.41383 (18) 0.13416 (14) 0.0359 (3)
C1 0.4576 (2) 0.83274 (18) 0.35330 (14) 0.0278 (3)
C2 0.8344 (2) 0.41590 (18) 0.15396 (14) 0.0279 (3)
C3 0.8544 (2) 0.51791 (19) 0.23960 (15) 0.0299 (3)
C4 0.5828 (2) 0.75504 (19) 0.24967 (15) 0.0308 (3)
C5 0.5012 (2) 0.74074 (17) 0.46204 (14) 0.0268 (3)
C6 0.9921 (2) 0.32078 (19) 0.09098 (14) 0.0301 (3)
C7 0.3241 (2) 0.97436 (19) 0.35238 (15) 0.0308 (3)
H7 0.294675 1.035203 0.278932 0.037*
C8 0.6557 (2) 0.59993 (18) 0.43202 (14) 0.0277 (3)
C9 0.2346 (2) 1.02311 (18) 0.46586 (15) 0.0296 (3)
C10 0.2783 (2) 0.92988 (19) 0.57536 (15) 0.0307 (3)
C11 0.4126 (2) 0.78582 (19) 0.57477 (15) 0.0311 (3)
H11 0.441158 0.722873 0.647340 0.037*
C12 1.1617 (2) 0.3293 (2) 0.11558 (16) 0.0362 (4)
H12 1.264843 0.266228 0.074564 0.043*
C13 1.0195 (2) 0.5247 (2) 0.26132 (16) 0.0358 (4)
H13 1.029106 0.593032 0.317801 0.043*
C14 1.1750 (2) 0.4291 (2) 0.19885 (17) 0.0384 (4)
H14 1.286909 0.434098 0.214366 0.046*
C15 0.9717 (3) 0.2223 (2) 0.00324 (17) 0.0396 (4)
H15 1.071413 0.157799 −0.040071 0.048*
C16 0.6562 (3) 0.3203 (2) 0.05023 (18) 0.0423 (4)
H16 0.542836 0.318805 0.034729 0.051*
C17 0.8036 (3) 0.2229 (2) −0.01724 (18) 0.0449 (4)
H17 0.787143 0.159521 −0.075263 0.054*

Source of material

The title compound, 5,6-dichloro-2-(quinolin-8-yl)isoindoline- 1,3-dione, has been synthesized according to the literature [5]. A mixture of 1.175 g 4,5-dichlorophthalic acid (5 mmol) and 1.44 g 8-aminoquinoline (10 mmol) in 2 mL DMF was heated at 393 K for 30 min. Then 30 mL ethanol (95%) was added. Any insoluble matter was removed by filtration. Crystals of the title compound were harvested after slowly evaporation of the filtrate, yield 56% (based on 8-aminoquinoline).

Experimental details

The structure was solved by direct methods with the shelxs- program. All hydrogen atoms were positioned with idealized geometry and refined isotropic (Uiso(H) = 1.2Ueq(C)) using a riding model with C—H = 0.93 Å.

Comment

Thalidomide, lenalidomide and phthalimides are famous for their biological activities [6]. Some 5,6–Di-chloride-substituted phthalimides, such as 5,6-di-chloro-2-(2-hydroxyphenyl)- isoindoline-1,3-dione [5], 5,6-dichloro-2-(3-methoxyphenyl) isoindoline-1,3-dione [7], 5,6-dichloro-2-(2-fluorophenyl)isoindoline-1,3-dione [8] and 2-(4-acetyl-2,6-dimethylphenyl)-5,6-dichloro-1H-iso-indole-1,3(2H)-dione [9] have been reported. There are also some crystal structures of N-quinolyl substituted phthalimides have been published, including 2-(quinolin-8-yl)-1H-isoindole-1,3(2H)-dione and its silver complex [10, 11], and 5-phenyl-2-(quinolin-8-yl)-1H-isoindole-1,3(2H)-dione [12]. Recently, two very similar structure, 4-chloro-2-(quinolin-8-yl)-isoindoline-1,3-dione [13] and 4-chloro-2-(quinolin-8-yl)-isoindoline-1,3-dione [14], have been reported. 5,6–Dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione crystalizes in P 1 ‾ , with one molecule in the asymmetric unit (see the Figure). The N-quinolyl residue and the isoindoline-1,3-dione are co-planar, respectively and the two residues are rotatet about the C-N bond with an angle of nearly 90°. All the bond lengths are similar to the reported results [5, 7], [8], [9], [10], [11], [12], [13], [14]. The molecules are linked by weak CH⋯N hydrogen bonds and van der Waals interactions.

Corresponding author: Xiaoping Xu, Thoracic and Cardiac Surgery, Naval Medical Center of PLA, Naval Medical University, Shanghai, China, E-mail:

  1. Author contributions: 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.

References

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Received: 2021-11-25
Accepted: 2022-01-15
Published Online: 2022-02-15
Published in Print: 2022-04-26

© 2022 Jie Chen et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
  4. The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
  5. Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
  6. Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
  7. Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
  8. The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
  9. Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
  10. The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
  11. The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
  12. Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
  13. The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
  14. Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
  15. The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
  16. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
  17. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
  18. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
  19. Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
  20. Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
  21. The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
  22. The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
  23. The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
  24. The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
  25. Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
  26. The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
  27. The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
  28. Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
  29. The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
  30. Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
  31. The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
  32. The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
  33. The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
  34. Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
  35. The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
  36. The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
  37. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
  38. Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
  39. Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
  40. Crystal structure of a second modification of Pachypodol, C18H16O7
  41. Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
  42. The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
  43. The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
  44. The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
  45. Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
  46. The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
  47. Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
https://doi.org/10.1515/ncrs-2021-0454
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
  4. The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
  5. Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
  6. Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
  7. Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
  8. The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
  9. Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
  10. The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
  11. The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
  12. Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
  13. The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
  14. Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
  15. The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
  16. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
  17. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
  18. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
  19. Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
  20. Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
  21. The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
  22. The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
  23. The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
  24. The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
  25. Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
  26. The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
  27. The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
  28. Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
  29. The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
  30. Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
  31. The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
  32. The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
  33. The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
  34. Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
  35. The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
  36. The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
  37. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
  38. Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
  39. Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
  40. Crystal structure of a second modification of Pachypodol, C18H16O7
  41. Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
  42. The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
  43. The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
  44. The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
  45. Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
  46. The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
  47. Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
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