Home Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
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Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6

  • Lin-Li Tang and Fei Zeng ORCID logo EMAIL logo
Published/Copyright: April 23, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 4

Abstract

C26H28N2O6, monoclinic, P21/c (no. 14), a = 15.962(9) Å, b = 14.828(8) Å, c = 9.929(5) Å, β = 93.303°, V = 2346(2) Å3, Z = 4, R gt(F) = 0.0515, wR ref(F 2) = 0.1621, T = 296(2) K.

CCDC no.: 2339004

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: Yellow needle
Size: 0.10 × 0.05 × 0.05 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 27.5°, >99 %
N(hkl)measured, N(hkl)unique, R int: 25,898, 5290, 0.031
Criterion for I obs, N(hkl)gt: I obs > 2σ (I obs), 3316
N(param)refined: 313
Programs: Bruker,1 SHELX 2
Table 2:

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

Atom x y z U iso*/U eq
O1 0.40194 (9) 0.43814 (12) 0.38300 (16) 0.0931 (5)
O2 0.46942 (9) 0.34548 (12) −0.13755 (15) 0.0847 (5)
O3 0.71889 (8) 0.47381 (9) 0.23339 (14) 0.0663 (4)
O4 0.77020 (8) 0.08449 (9) 0.33455 (14) 0.0649 (4)
O5 1.07840 (9) 0.17698 (12) 0.16670 (14) 0.0911 (5)
O6 1.00535 (8) 0.09394 (9) 0.68705 (13) 0.0666 (4)
N1 0.66014 (8) 0.34255 (10) 0.13973 (14) 0.0499 (4)
N2 0.82677 (8) 0.21630 (9) 0.42968 (14) 0.0491 (4)
C1 0.31991 (16) 0.4364 (2) 0.4280 (3) 0.1002 (8)
H1A 0.284725 0.476076 0.373233 0.150*
H1B 0.320889 0.455964 0.520308 0.150*
H1C 0.298174 0.376145 0.421298 0.150*
C2 0.41217 (12) 0.41349 (13) 0.2511 (2) 0.0622 (5)
C3 0.34777 (12) 0.39277 (13) 0.1581 (2) 0.0676 (6)
H3 0.292457 0.394701 0.182641 0.081*
C4 0.36530 (12) 0.36927 (13) 0.0290 (2) 0.0680 (6)
H4 0.321518 0.354623 −0.032984 0.082*
C5 0.44699 (11) 0.36701 (13) −0.01047 (19) 0.0569 (5)
C6 0.51281 (10) 0.38739 (11) 0.08316 (18) 0.0511 (4)
C7 0.49396 (11) 0.41034 (13) 0.21263 (19) 0.0585 (5)
H7 0.537443 0.424040 0.275689 0.070*
C8 0.40582 (16) 0.3354 (2) −0.2396 (3) 0.1031 (9)
H8A 0.430248 0.319873 −0.322599 0.155*
H8B 0.375455 0.391061 −0.250907 0.155*
H8C 0.368149 0.288476 −0.215229 0.155*
C9 0.60201 (10) 0.38637 (13) 0.04114 (18) 0.0564 (5)
H9A 0.603871 0.355180 −0.044514 0.068*
H9B 0.620305 0.447951 0.027873 0.068*
C10 0.61561 (12) 0.18480 (14) 0.0795 (2) 0.0649 (5)
H10A 0.557432 0.200249 0.084018 0.097*
H10B 0.625008 0.125237 0.115120 0.097*
H10C 0.630585 0.186481 −0.012750 0.097*
C11 0.66760 (10) 0.25007 (11) 0.15955 (17) 0.0473 (4)
C12 0.72822 (10) 0.23661 (11) 0.26063 (17) 0.0469 (4)
C13 0.71545 (10) 0.39170 (12) 0.23009 (17) 0.0486 (4)
C14 0.75946 (10) 0.32170 (11) 0.30726 (16) 0.0460 (4)
C15 0.77246 (10) 0.16676 (12) 0.33795 (17) 0.0481 (4)
C16 0.81921 (10) 0.30892 (11) 0.40929 (17) 0.0474 (4)
C17 0.86911 (12) 0.37555 (14) 0.4898 (2) 0.0674 (5)
H17A 0.847157 0.380979 0.577426 0.101*
H17B 0.866155 0.432987 0.445148 0.101*
H17C 0.926499 0.356047 0.499182 0.101*
C18 0.88477 (11) 0.17168 (13) 0.52602 (17) 0.0543 (5)
H18A 0.860236 0.114934 0.552262 0.065*
H18B 0.891770 0.208914 0.606204 0.065*
C19 0.97001 (10) 0.15318 (11) 0.47421 (17) 0.0483 (4)
C20 1.03000 (11) 0.11051 (11) 0.55933 (18) 0.0501 (4)
C21 1.06607 (16) 0.05861 (18) 0.7816 (2) 0.0944 (8)
H21A 1.087992 0.003348 0.747575 0.142*
H21B 1.040674 0.047116 0.865211 0.142*
H21C 1.110857 0.101328 0.796302 0.142*
C22 1.10663 (11) 0.08756 (12) 0.5126 (2) 0.0590 (5)
H22 1.146015 0.057825 0.569160 0.071*
C23 1.12558 (11) 0.10849 (13) 0.3814 (2) 0.0613 (5)
H23 1.177317 0.092466 0.350057 0.074*
C24 1.06742 (11) 0.15307 (13) 0.29799 (19) 0.0596 (5)
C25 0.99014 (11) 0.17481 (13) 0.34516 (18) 0.0578 (5)
H25 0.950901 0.204698 0.288477 0.069*
C26 1.15943 (15) 0.17291 (18) 0.1203 (2) 0.0905 (7)
H26A 1.159134 0.197260 0.030737 0.136*
H26B 1.177801 0.111273 0.119309 0.136*
H26C 1.196975 0.207395 0.179190 0.136*

1 Source of material

A dichloromethane (12 mL) solution of (2,5-dimethoxyphenyl)methanamine (1.0 g, 6 mmol) and triethylamine (0.03 mL, 8 mmol) was added to a 50 ml round bottom flask and cooled to 0 °C. At this temperature, fumaric chloride (0.7 ml, 4 mmol) in dichloromethane (6 mL) was added drop by drop within 1 h, and white smoke was observed, and a large amount of white precipitation was observed in the reaction mixture. After removing the ice bath, reaction mixture was stirred at room temperature overnight. After the reaction was completed, the solution was filtered first, and the obtained white solid was washed with sodium hydroxide (1 mol/L) and hydrochloric acid (1 mol/L) with cold dichloromethane. After vacuum drying, the product N1,N4-bis(2,5-dimethoxybenzyl)fumaramide (1.24 g, 3 mmol) was obtained as a white solid. Compound N1,N4-bis(2,5-dimethoxybenzyl)fumaramide (8.284 g, 20 mmol) and isopropyl acetate (150 mL) were added to a 500 mL round bottom flask. Then a dimethylformamide solution of p-toluenesulfonic acid (20 mL, 0.10 mol/L) was added, and the reaction mixture was heated at 105 °C (oil bath) in a nitrogen atmosphere, stirring for 12 h. It was observed that the white solid gradually dissolved, and the solution turned brown and yellow. After the reaction, it was cooled to room temperature, and the reaction mixture was concentrated under reduced pressure to remove most of the solution. The residue was dissolved in ethyl acetate (300 mL) and washed by 5 % HCl aqueous solution (200 mL) twice, saturated NaHCO3 solution (200 mL) and water. The organic phase was separated, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography (dichloromethane/ethyl acetate 10:1) and vacuum dried to afford N1,N4-diacetyl–N1,N4-bis(2,5-dimethoxybenzyl)fumaramide (7.47 g, 15 mmol). N1,N4-diacetyl–N1,N4-bis(2,5-dimethoxybenzyl)fumaramide (2.8 g, 5.63 mmol), acetonitrile (50 mL), PPh3 (1.495 g, 5.7 mmol) and pyridinium p-toluene sulfonate (0.7288 g, 2.9 mmol) were added to a 100 mL round bottom flask. The reaction mixture was stirred at 100 °C (oil bath) for 10 h. After the reaction, it was cooled to room temperature, and the yellow solid was separated. The reaction mixture was concentrated under reduced pressure to remove the acetonitrile solvent. The residual solid was dissolved in dichloromethane (200 mL) and extracted with water (200 mL). The organic phase was separated, dried with anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (dichloromethane/ethyl acetate = 8:1) to produce 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (1.7 g, 3.66 mmol) as a green solid. Crystals of the title compound were obtained by slow vaporization of a solution in CH2Cl2 within one week.

2 Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

3 Comment

Diketopyrrolopyrrole (DPP), which was discovered in 1974, has become one of the most widely used prototypical π-cores for organic electronic devices and high performance pigments. 3 – 6 The conventional synthesis of the DPP core involves heating a mixture of aromatic nitrile (Ar–CN) and succinic acid ester in the presence of a strong base such as potassium tert-butoxide (KOtBu), giving rise to a DPP unit bearing two aromatic rings at the 3,6-positions. 7 , 8 In 2019, Scott and co-workers reported the efficient synthesis of a new DPP scaffold, 2,5-dibutyl-3,6-dimethyl-1H,2H,4H,5H-pyrrolo [3,4-c]pyrrole-1,4-dione, using tandem cyclization of N1,N4-diacetyl–N1,N4-dibutylfumaramide. 9 Recently, Tan’s group reported the synthesis of an N-substituted DPP derivative Ph–DPP by Scott’s method and obtained molecule exhibited quite sensitive chromogenic and fluorescent responses toward F′. 10 However, none of the diketopyrrole derivatives reported by Scott and Tan have a single crystal structure. Herein, we reported the synthesis of a new DPP derivative 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo [3,4-c]pyrrole-1,4-dione, which may enrich the DPP chemistry. The title compound, built up by the C26H28N2O6 molecules, has been synthesized. The single-crystal structure verifies that all bond lengths are in normal ranges [11].

Corresponding author: Fei Zeng, Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, P.R. China, E-mail:

Funding source: General Scientific Research Project of Hunan University of Science and Engineering

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

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

  3. Research funding: The work was supported by General Scientific Research Project of Hunan University of Science and Engineering.

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Received: 2024-03-09
Accepted: 2024-04-11
Published Online: 2024-04-23
Published in Print: 2024-08-27

© 2024 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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https://doi.org/10.1515/ncrs-2024-0122
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O ″)cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
  19. The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
  21. Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
  22. Crystal structure of poly[(μ3-5-bromoisophthalato-κ4 O,O′ :O″,O‴)-(μ2-1,2-bis(1,2,4-triazole-1-ylmethyl)benzene-κ2 N:N′)cobalt(II)], C20H15BrCoN6O4
  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O ′:O ″,O ‴)-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N′)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
  31. Crystal structure of poly[octakis(μ-oxido)-tris(μ-1,1′-[[1,1′-biphenyl]-4,4′-diylbis(methylene)]bis(1H-imidazole))-tetrakis(oxido)-tetra-vanadium-dimanganese(II)dihydrate], C30H29MnN6O7V2
  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
  33. Crystal structure of benzo[d][1,3]dioxol-5-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H20O5
  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
  35. The crystal structure of N-(2-((2-methoxynaphthalen-1-yl)ethynyl)phenyl)-4-methylbenzenesulfonamide, C26H21NO3S
  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
  37. The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
  40. Synthesis, crystal structure and nonlinear optical property of 1-((propan-2-ylideneamino)oxy)propan-2-yl-4-methylbenzenesulfonate, C13H19O4NS
  41. The crystal structure of N,N-(ethane-1,1-diyl)dibenzamide, C16H16N2O2
  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
  43. The crystal structure of fac-tricarbonyl(bis(3,5-dimethyl-4H-pyrazole)-κ1 N)-((nitrato)-κ1 O)-rhenium(I)— 3,5-dimethyl-4H-pyrazole(1/1), C18H23N7O6Re
  44. The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5
  45. Crystal structure of tetraethylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  46. Crystal structure of 1-cyclohexyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, C22H27NO4
  47. The crystal structure of catena-poly(μ2-1,4-bis-(1H-imidazol-1-yl)benzene-copper(I)) dichloridocopper(I), {[CuC12H10N4]+[CuCl2]−} n
  48. The crystal structure of propane-1-aminium-2-carbamate, C4H10N2O2
  49. Crystal structure of 5,6,3′,4′,5′-pentamethoxy-flavone dihydrate, C20H24O9
  50. Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
  51. Crystal structure of methyl (3R)-1-(2-bromo-4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride hydrate, C19H19BrClFN2O3
  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
  53. The crystal structure of 1-cyclohexyl-3-(p-tolyl)urea, C14H20N2O
  54. Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P
  55. The crystal structure of ethyl 3-(1-methyl-1H-indole-2-carbonyl)-2-phenylquinoline-4-carboxylate, C28H22N2O3
  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 −)
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N ′-dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
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