Startseite Crystal structure of 2,6-bis(2-(pyridin-3-yl)ethyl)pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone, C24H18N4O4
Artikel Open Access

Crystal structure of 2,6-bis(2-(pyridin-3-yl)ethyl)pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone, C24H18N4O4

  • Yu Jeong Jeong , Juhyeon Park , Ahreum Min , Tae Ho Kim ORCID logo EMAIL logo und Myong Yong Choi EMAIL logo
Veröffentlicht/Copyright: 18. Januar 2021

Abstract

C24H18N4O4, monoclinic, P21/c (no. 14), a = 16.5930(5) Å, b = 5.7298(2) Å, c = 20.8714(6) Å, β = 99.8620(10)°, V = 1955.02(11) Å3, Z = 4, Rgt(F) = 0.0415, wRref(F2) = 0.1115, T = 193 K.

CCDC no.: 2052124

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:Yellow plate
Size:0.79 × 0.20 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.10 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:27.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:33246, 4504, 0.034
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3667
N(param)refined:289
Programs:Bruker [1], SHELX [2], [, 3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
O10.88225 (7)0.1089 (2)0.00346 (5)0.0389 (3)
O20.80184 (7)0.7719 (2)−0.11129 (5)0.0368 (3)
O30.68164 (7)0.38724 (19)0.20650 (5)0.0372 (3)
O40.59838 (6)1.04529 (19)0.09029 (5)0.0361 (3)
N11.13414 (10)0.1282 (3)−0.18454 (11)0.0643 (5)
N20.85154 (7)0.4217 (2)−0.06601 (5)0.0307 (3)
N30.63232 (7)0.7386 (2)0.16195 (5)0.0280 (3)
N40.62521 (9)1.3046 (2)0.40612 (6)0.0365 (3)
C11.08607 (11)0.1844 (3)−0.14137 (9)0.0446 (4)
H11.08080.0744−0.10830.054*
C21.14040 (12)0.2881 (5)−0.22962 (10)0.0648 (7)
H21.17360.2532−0.26120.078*
C31.10243 (12)0.4969 (5)−0.23317 (8)0.0584 (6)
H31.10990.6060−0.26590.070*
C41.05337 (10)0.5494 (3)−0.18930 (9)0.0438 (4)
H41.02580.6952−0.19150.053*
C51.04381 (8)0.3914 (3)−0.14193 (7)0.0314 (3)
C60.99111 (11)0.4391 (4)−0.09156 (9)0.0591 (6)
H6A0.99120.6088−0.08260.071*
H6B1.01470.3588−0.05060.071*
C70.90325 (9)0.3574 (3)−0.11305 (7)0.0342 (3)
H7A0.88100.4280−0.15570.041*
H7B0.90260.1857−0.11840.041*
C80.84580 (8)0.2889 (3)−0.01128 (6)0.0289 (3)
C90.78840 (8)0.4176 (2)0.02392 (6)0.0253 (3)
C100.76340 (8)0.6194 (2)−0.01122 (6)0.0253 (3)
C110.80505 (9)0.6254 (3)−0.06927 (6)0.0285 (3)
C120.76313 (8)0.3623 (2)0.08202 (6)0.0259 (3)
H120.78010.22440.10590.031*
C130.71116 (8)0.5246 (2)0.10233 (6)0.0243 (3)
C140.68582 (8)0.7257 (2)0.06718 (6)0.0247 (3)
C150.71022 (8)0.7801 (3)0.00862 (6)0.0263 (3)
H150.69200.9158−0.01580.032*
C160.67554 (8)0.5295 (3)0.16336 (6)0.0268 (3)
C170.63349 (8)0.8636 (3)0.10483 (6)0.0267 (3)
C180.59323 (9)0.8217 (3)0.21534 (7)0.0335 (3)
H18A0.55630.69940.22720.040*
H18B0.55990.96170.20110.040*
C190.65698 (9)0.8821 (3)0.27433 (6)0.0287 (3)
H19A0.68730.73850.28990.034*
H19B0.69660.99340.26090.034*
C200.62214 (8)0.9872 (2)0.32979 (6)0.0250 (3)
C210.56593 (9)0.8722 (3)0.36054 (7)0.0311 (3)
H210.54590.72290.34570.037*
C220.53917 (9)0.9757 (3)0.41287 (7)0.0345 (3)
H220.49970.90050.43380.041*
C230.57066 (9)1.1898 (3)0.43421 (7)0.0349 (3)
H230.55271.25890.47070.042*
C240.64907 (9)1.2038 (3)0.35471 (7)0.0309 (3)
H240.68701.28590.33380.037*

Source of material

A mixture of pyromellitic dianhydride (0.218 g, 1 mmol) and 3-(2-aminoethyl)pyridine (0.234 mL, 2 mmol) in toluene (1 mL) and quinoline (3 mL) was heated at 473 K with stirring for 1 h. Upon cooling to room temperature, brown solid was precipitated and dark liquid was filtered off. The solid was successively washed with water, methanol, and diethyl ether and crude product was obtained. After dissolving in dichloromethane, the product was purified by column chromatography over silica gel eluting with a gradient of ethyl acetate 100% to give the light brown solid. Yield: 0.239 g (56%). A small amount of the title compound was dissolved in acetone and slow evaporation yielded yellow crystals. NMR data have been measured with a Bruker DRX300 spectrometer. IR measurements have been made with a Thermo Scientific Nicolet iS10 IR spectrometer at the Core–Facility Center for Photochemistry & Nanomaterials.

1H NMR (300 MHz, ppm, DMSO-d6, r.t.): 8.41 (d, 2H, H2, H23); 8.39 (d, 2H, H1, H24); 8.16 (s, 2H, H12, H15); 7.69–7.65 (m, 2H, H4, H21); 7.30–7.26 (d, 2H, H3, H22); 3.91–3.87 (t, 2H, H7, H18); 2.99–2.95 (t, 2H, H6, H19).

13C NMR (75.4 MHz, ppm, DMSO-d6, r.t.): 165.99, 149.78, 147.83, 136.82, 136.33, 123.49, 117.32, 44.59 and 30.73.

IR (n, cm−1): 3455(m); 3095 (m); 3031 (m); 2965 (s); 2941 (s); 2847(s); 1761(s); 1700(s); 1576 (s).

Experimental details

The C-bound H atoms were geometrically placed (C–H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C).

Comment

Pyromellitic diimide derivatives would be important compounds in terms of their optoelectronic and electrochemical properties [5]. In the extension of the study of pyromellitic diimide derivatives [6], the title compound was synthesized by the similar method for synthesizing N, N′-bis[3-(methylsulfanyl)propyl]-1,8:4,5-naphthalenetetracarboxylic diimide [7]. Similar to the previously reported compounds of N, N′-bis(2-pyridylethyl)pyromellitic diimide [8], this title compound also has heterocyclic groups separated by ethylene moieties. This ethylene connection allows free rotation of the terminal rings. All bond lengths and bond angles are normal and similar to those observed for similar crystal structures [8], [, 9].

In the crystal structure, the m-pyridyl groups on both sides of the central pyromellitic diimide plane are of a syn form. The dihedral angles between the mean planes of the central pyromellitic diimide ring [r.m.s. deviation = 0.0432 Å] and the terminal m-pyridyl groups are 7.84(8) and 56.66(4)°. Four C–H⃛N, C–H⃛O hydrogen bonds and four weak intermolecular ππ interactions further stabilize the crystal structure. The distances of each hydrogen bond are [C1–H1⃛O1i = 2.41 Å, C15–H15⃛N4ii = 2.42 Å, C19–H19⃛O2)iii = 2.55 Å, C19–H19B⃛O3iv = 2.52 Å for symmetry operations (i): 2 − x, −y, −z; (ii): x, 5/2 − y, −1/2 + z (iii): x, 3/2 − y, 1/2 + z and (iv): x, 1 + y, z] and the distances of each ππ interaction are [Cg(N2–C11)⃛Cg(N4–C24)v = 3.7622 (9) Å, Cg(N3–C17)⃛Cg(N2–C2)vi = 3.9723 (10) Å, Cg(N2–C2)⃛Cg(C9–C12)vii = 3.7444(9) Å, Cg(N4–C24)⃛Cg(C9–C12)iii = 3.8904(8) Å for symmetry operations (v): x, 3/2 − y, −1/2 + z; (vi): 2 − x, 1 − y, −z; and (vii): 2 − x, 1 − y, −z.].


Corresponding authors: Myong Yong Choi and Tae Ho Kim, Department of Chemistry (BK21 FOUR) and Research Institute of Natural Sciences, Gyeongsang National University, Jinju52828, Republic of Korea, E-mail: , E-mail:

Funding source: National Research Facilities & Equipment Center (NFEC)

Award Identifier / Grant number: 2019R1A6C1010042

Award Identifier / Grant number: 2018R1D1A3B07042615

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

  2. Research funding: Korea Basic Science Institute (KBSI), National Research Facilities & Equipment Center (NFEC) grant funded by the Korea government (Ministry of Education) (No. 2019R1A6C1010042). Dr. T. H. Kim acknowledge the financial support from National Research Foundation of Korea (NRF), (2018R1D1A3B07042615).

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

References

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Received: 2020-12-10
Accepted: 2020-12-23
Published Online: 2021-01-18
Published in Print: 2021-05-26

© 2020 Yu Jeong Jeong et al., 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. The crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxidoethylidene)benzohydrazonato-κ5N,O,O′:N′,O′′)hexkis(pyridine-κ1N)trinickel(II) - pyridine (1/1), C63H57Cl2N13Ni3O6
  4. Crystal structure of [(μ2-succinato κ3O,O′:O′′)-bis-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane)]dinickel(II)] diperchlorate, dihydrate C36H82Cl2N8Ni2O15
  5. Crystal structure of catena-poly[aquabis(3-nitrobenzoato-κ2O:O′)-(μ2-pyrazine-N: N′)cadmium(II)], C18H14N4O9Cd
  6. Crystal structure of 4-(2,2-difluoroethyl)-2,4,6-trimethylisoquinoline-1,3(2H,4H)-dione, C14H15F2NO2
  7. The crystal structure of thioxanthen-9-one-10,10-dioxide, C13H8O3S – a second polymorph
  8. Crystal structure of (E)-2-((2-methoxy-3-pyridyl)methylene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  9. The crystal structure of diaquahydrogen 2,5-dimethylbenzenesulphonate, C8H14O5S
  10. The crystal structure of N-(4-(cyclohexylimino)pent-2-en-2-yl)cyclohexanamine, C17H30N2
  11. The twinned crystal structure of 1,3-phenylenedimethanaminium dibromide, C8H14Br2N2
  12. Crystal structure of 2,4,7,9-tetranitro-10H-benzofuro[3,2-b]indole – dimethyl sulfoxide (1/1), C16H11N5O10S
  13. Crystal structure of 2,6-bis(2-(pyridin-3-yl)ethyl)pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone, C24H18N4O4
  14. The crystal structure of 3,4-dichlorobenzoic acid chloride, C7H3Cl3O
  15. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-k2S:S)zinc(II), C26H18N6ZnS4
  16. Crystal structure of tetrakis(μ-naphthalene-1-carboxylato-κ2O,O′)bis(methanol)copper(II), C46H36Cu2O10
  17. Crystal structure of 9-methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one, C14H13NO
  18. Crystal structure of bis(amino(carbamothioylamino)methaniminium) 3-nitrophthalate monohydrate, C12H19N9O7S2
  19. Crystal structure of 3,3′-(1,2-phenylene-bis(methylene))bis(1-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate), C18H24F12N4P2
  20. The crystal structure of 5-hydroxy-6,8-dimethoxy-2-methyl-4H-benzo[g]chromen-4-one– rubrofusarin B, C16H14O5
  21. The crystal structure of bis(ethanol-kO)- bis(6-aminopicolinato-k2N,O)manganese(II), C16H22O6N4Mn
  22. The crystal structure of 3,3′-((carbonylbis(azanediyl))bis(ethane-2,1-diyl)) bis(1-methyl-1H-benzo[d]imidazol-3-ium) tetrafluoroborate monohydrate, C21H28N6O3B2F8
  23. Crystal structure of dimethanol-dichlorido-bis( μ2-2-(((1,5-dimethyl-3-oxo-2- phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato- κ4O:O,O′,N)dinickel (II), C20H24ClNiN3O4
  24. The crystal structure of methyl 5-(trifluoromethyl)-1H-pyrrole-2-carboxylate, C7H6F3NO2
  25. Crystal structure of (OC‐6‐13)‐aqua‐tris (3‐bromopyridine‐κ1N)‐bis(trifluoroacetato‐κ1O)cadmium(II) C19H14Br3CdF6N3O5
  26. Crystal structure of methyl (E)-3-(4-(2-ethoxy-2-oxoethoxy)phenyl) acrylate, C14H16O5
  27. Crystal structure of methyl 4-acetoxy-3,5-dimethoxybenzoate, C12H14O6
  28. The crystal structure of 2-(1H-benzimidazol-2-yl)-3-bromo-5-chlorophenol, C13H8BrClN2O
  29. The crystal structure of bis(μ2-5-chloro-N-(2-methyl-1-oxidopropylidene)-2-oxidobenzohydrazonate-κ5N,O,O′:N′,O′′)pentakis(pyridine-κ1N)tricopper(II), C47H45Cl2N9Cu3O6
  30. Synthesis and crystal structure of catena-poly[aqua-bis(nitrato-κ2O:O′)- (μ2-((1 H-imidazol-1-yl)methyl)benzene-κ2 N,N′)-H2O-κ2O]cadmium(II), C14H16N6O7Cd
  31. The crystal structure of pentakis(carbonyl)-{μ-[2,3-bis(sulfanyl)propan-1-olato]}-(triphenylphosphane)diiron (FeFe)C26H21Fe2O6PS2
  32. Crystal structure of ethyl-2-(3-benzoylthioureido)propanoate, C13H16N2O3S
  33. Crystal structure of 2-methoxy-4b,5,14,15-tetrahydro-6H-isoquinolino[2′,1′:1,6] pyrazino[2,3-b]quinoxaline, C19H18N4O
  34. Crystal structure of 2,2′-[ethane-1,2-diylbis(azanylylidenemethylylidene)]bis(6-chlorophenol), C16H14Cl2N2O2
  35. The crystal structure of (Z)-3-((2-(2-(2-aminophenoxy)ethoxy)phenyl)amino)-1-phenylbut-2-en-1-one, C24H24N2O3
  36. The crystal structure of 10-(3,5-di(pyridin-4-yl)phenyl)-10H-phenoxazine dihydrate, C28H23N3O3
  37. Crystal structure of poly[dipoly[aqua-di(µ2-pyrazin-2-olato-κ2N:N′) zinc(II)], C8H8N4O3Zn
  38. Crystal structure of poly[tetra(μ2-cyanido-κ2N:O)-bis(N,N-dimethylformamide-κO)-manganese(II)-platinum(II)], C10H14MnN6O2Pt
  39. The crystal structure of aqua-chlorido-6,6′-((ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dichlorophenolato-κ4N,N′,O,O′)manganese(III), C16H12Cl5MnN2O3
  40. Crystal structure of [di(µ2-cyanido)-dicyanido-bis(dimethyl sulfoxide-κO)- bis(2,2′-(ethane-1,2-diylbis(azanylylidenemethanylylidene))diphenolato-κ4,N,N′,O,O′)- dimanganese(III)-platinum(II)], C40H40Mn2N8O6PtS2
  41. The crystal structure of (azido)-κ1N-6,6′-((cyclohexane-1,2-diylbis(azanylylidene)) bis(methanylylidene))bis(3-bromophenolato-κ4N,N,O,O)-(methanol)-manganese(III)–methanol(1/1), C22H26Br2MnN5O4
  42. Crystal structure of 7-chloro-N-(4-iodobenzyl)-1,2,3,4-tetrahydroacridin-9-amine, C20H18ClIN2
  43. Crystal structure of catena-poly[(1,4,8,11-tetraazacyclotetradecane-κ4N,N,N,N′′′)-bis(μ2-thiocyanato-κ2N:S)-bis(thiocyanato-κS)-nickel(II)palladium(II)], C14H24N8NiPdS4
  44. Crystal structure of 3-chloro-4-(4-ethylpiperazin-1-yl)aniline monohydrate, C12H20ClN3O
  45. Crystal structure of the 2D coordination polymer poly[diaqua-bis(μ2-3- methoxyisonicotinato-κ2N:O)cobalt(II)] — dimethylformamide (1/1), C20H30CoN4O10
  46. Crystal structure of 4-[(5-chloro-2-hydroxybenzylidene)amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione, C12H13ClN4OS
  47. Crystal structure of N-(5-(2-(benzyl(1-(4-methoxyphenyl)propan-2-yl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide, C33H36N2O4
  48. Crystal structure of 3-(methoxycarbonyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid, C9H12O5
  49. The crystal structure of 1-((dimethylamino)(3-nitrophenyl)methyl)naphthalen-2-ol, C19H18N2O3
  50. Crystal structure of catena-poly[di(μ2-cyanido-κ2C:N)-dicyanido-tetrakis(dimethyl sulfoxide-κO)-manganese(II)-platinum(II)], C12H24MnN4O4PtS4
  51. Crystal structure of 4-amino-N-(2-pyrimidinyl)benzenesulfonamide–1,4-dioxane (1/1), C14H18N4O4S
  52. Crystal structure of bis{1-[(benzotriazol-1-yl)methyl]-1H-1,3-(2-methyl-imidazol)}di-chloridomercury(II), [Hg(C11H11N5)2Cl2], C22H22N10Cl2Hg
  53. Crystal structure of 2, 3-bis((4-methylbenzoyl)oxy) succinic acid–N, N-dimethylformamide (1/1), C23H25NO9
  54. Crystal structure of catena-poly[bis(4-(4-carboxyphenoxy)benzoato-κ1O)-μ2-(1,4-bis(1-imidazolyl)benzene-κ2N:N′)cobalt(II)], C40H28N4O10Co
  55. Crystal structure of 1H-imidazol-3-ium poly[aqua-(μ4-glutarato-κ6O,O′:O′:O′′,O′′′:O′′′)-(nitrato-κ2O,O′)strontium(II)], C8H13N3O8Sr
  56. Crystal structure of (R)-6-(benzo[b]thiophen-5-yl)-2-methyl-2,6-dihydrobenzo [5,6] silino[4,3,2-cd]indole, C23H17NSSi
  57. Crystal structure of catena-poly[bis(μ2-thiocyanato-κ2N:S)-(2-(5-methyl-1H-pyrazol-3-yl)pyridine-κ2N,N′)cadmium(II)]–dioxane (1/1), C15H17CdN5O2S2
  58. Crystal structure of poly[aqua-(μ2-1,4-bis(2′-carboxylatophenoxy)benzene-κ2O:O′)-(μ2-4,4′-bipyridione-κ2N:N′)cadmium(II)] monhydrate, C30H22CdN2O7⋅H2O
  59. Crystal structure of catena-poly[tetraaqua-(μ2-4,4′-bipyridine-k2N:N′)-bis(μ2-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-k4O,O′:O″,O′″)dicadmium(II)] dihydrate, C20H20NO7Cd
  60. Crystal structure of 1‐tert‐butyl‐3‐(2,6‐diisopropyl‐4‐phenoxyphenyl)‐2-methylisothiourea, C24H34N2OS
  61. Crystal structure of catena-poly[triaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ1O)cobalt(II)] — N,N′-dimethylformamide (1/1), C28H34N8O8Co
  62. Crystal structure of tetraaqua-bis(1,4-di(1H-imidazol-1-yl)benzene-κ1N)manganese(II) 2,3-dihydroxyterephthalate, C32H32MnN8O10
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