Startseite 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
Artikel Open Access

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

  • Du Yuchang ORCID logo EMAIL logo , Li Guoxiang , Zeng Guimei , He Xiaobing , Zou Shengqin und Chen Zuliang
Veröffentlicht/Copyright: 27. Mai 2024

Abstract

C28H29NO9, triclinic, P1̄ (no. 2), a = 9.1736(7) Å, b = 12.4005(9) Å, c = 13.0593(9) Å, α = 67.098(7)°, β = 72.187(6)°, γ = 88.103(6)°, V = 1296.61(19) Å3, Z = 2, Rgt (F) = 0.0444, wRref (F 2) = 0.1119, T = 200 K.

CCDC no.: 2277072

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: 0.14 × 0.12 × 0.11 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.10 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 25.0°, >99 %
N(hkl)measured, N(hkl)unique, R int: 8519, 4565, 0.024
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3684
N(param)refined: 349
Programs: Bruker 1 , SHELX 2 5

Table 2:

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

Atom x y z U iso*/U eq
O1 0.31077 (17) 0.00347 (12) 1.00678 (11) 0.0418 (4)
O2 0.35081 (17) 0.18545 (12) 0.99459 (11) 0.0406 (4)
O3 0.46696 (14) 0.24418 (10) 0.76488 (10) 0.0270 (3)
O4 0.20314 (17) 0.34669 (12) 0.75378 (13) 0.0470 (4)
O5 0.06504 (14) 0.19169 (11) 0.91138 (11) 0.0336 (3)
O6 0.64205 (17) 0.33155 (13) 0.11330 (11) 0.0436 (4)
O7 0.58472 (15) 0.42285 (11) 0.23653 (12) 0.0366 (3)
O8 0.97578 (16) 0.21278 (12) 0.29091 (12) 0.0416 (4)
O9 0.94753 (15) 0.37543 (12) 0.14619 (12) 0.0421 (4)
N1 0.19246 (16) 0.08992 (13) 0.72429 (12) 0.0255 (3)
C1 0.4821 (2) 0.15239 (14) 0.44267 (14) 0.0230 (4)
C2 0.40624 (19) 0.13072 (14) 0.55997 (14) 0.0212 (4)
C3 0.2479 (2) 0.10220 (14) 0.60718 (14) 0.0230 (4)
C4 0.1612 (2) 0.08987 (15) 0.54095 (15) 0.0272 (4)
H4 0.055576 0.069134 0.573519 0.033*
C5 0.2371 (2) 0.10947 (16) 0.42502 (15) 0.0287 (4)
H5 0.181573 0.101623 0.379089 0.034*
C6 0.3935 (2) 0.14038 (15) 0.37640 (15) 0.0269 (4)
H6 0.441392 0.153535 0.298108 0.032*
C7 0.46702 (19) 0.13496 (14) 0.65335 (14) 0.0214 (4)
H7 0.551210 0.084860 0.661333 0.026*
C8 0.32538 (19) 0.08680 (15) 0.76536 (14) 0.0237 (4)
H8 0.335722 0.006184 0.815623 0.028*
C9 0.3265 (2) 0.17128 (15) 0.82681 (14) 0.0240 (4)
C10 0.5116 (2) 0.25848 (15) 0.64391 (14) 0.0234 (4)
H10 0.451607 0.316139 0.602594 0.028*
C11 0.6795 (2) 0.30048 (15) 0.58832 (14) 0.0236 (4)
C12 0.7353 (2) 0.38419 (15) 0.47457 (15) 0.0280 (4)
H12 0.667157 0.418371 0.433734 0.034*
C13 0.8915 (2) 0.41744 (16) 0.42115 (16) 0.0321 (5)
H13 0.926959 0.472525 0.344074 0.039*
C14 0.9962 (2) 0.37044 (16) 0.47998 (17) 0.0305 (4)
C15 0.9387 (2) 0.28999 (16) 0.59579 (17) 0.0313 (4)
H15 1.006164 0.259594 0.638244 0.038*
C16 0.7832 (2) 0.25432 (16) 0.64902 (16) 0.0293 (4)
H16 0.747681 0.199032 0.726012 0.035*
C17 1.1661 (2) 0.40510 (19) 0.4203 (2) 0.0439 (5)
H17A 1.206570 0.361059 0.373280 0.066*
H17B 1.216732 0.388736 0.478385 0.066*
H17C 1.183425 0.487632 0.371195 0.066*
C18 0.3272 (2) 0.10733 (17) 0.95337 (15) 0.0268 (4)
C19 0.3669 (3) 0.1393 (2) 1.11005 (17) 0.0479 (6)
H19A 0.431265 0.075883 1.117463 0.072*
H19B 0.267397 0.110937 1.168027 0.072*
H19C 0.412804 0.200448 1.121469 0.072*
C20 0.1924 (2) 0.24866 (16) 0.82420 (15) 0.0269 (4)
C21 −0.0715 (2) 0.2540 (2) 0.9165 (2) 0.0470 (6)
H21A −0.084375 0.286504 0.840372 0.070*
H21B −0.061046 0.316228 0.940867 0.070*
H21C −0.159779 0.200423 0.971704 0.070*
C22 0.6488 (2) 0.18117 (15) 0.39092 (15) 0.0246 (4)
H22 0.708371 0.140536 0.437253 0.030*
C23 0.7238 (2) 0.26009 (15) 0.28366 (15) 0.0253 (4)
C24 0.8947 (2) 0.27716 (17) 0.24364 (16) 0.0293 (4)
C25 1.1124 (2) 0.4010 (2) 0.0991 (2) 0.0615 (7)
H25A 1.138099 0.478055 0.036910 0.092*
H25B 1.156482 0.343791 0.069021 0.092*
H25C 1.152291 0.398204 0.159864 0.092*
C26 0.6463 (2) 0.33974 (16) 0.20107 (15) 0.0273 (4)
C27 0.5109 (3) 0.50899 (19) 0.1619 (2) 0.0496 (6)
H27A 0.582197 0.545211 0.084030 0.074*
H27B 0.478398 0.567989 0.192381 0.074*
H27C 0.422977 0.470888 0.159923 0.074*
C28 0.0596 (2) 0.00615 (18) 0.80435 (16) 0.0394 (5)
H28A −0.027423 0.028295 0.777222 0.059*
H28B 0.036956 0.005944 0.881233 0.059*
H28C 0.081713 −0.071059 0.807429 0.059*

1 Source of material

A flame-dried schlenk tube (25 mL) was evacuated and recharged with N2 for 3 times. Under N2 atmosphere, the tube was charged with 10 mol% Zn(NTf2)2, 4 Å M. S. (60 mg), dimethyl 2-((1-methyl-1H-indol-4-yl)methylene)malonate (0.3 mmol, 90 mg, synthesized by the reported procedure earlier 1 ), dimethyl 3-(p-tolyl)oxirane-2,2-dicarboxylate (0.45 mmol, 123 mg, synthesized by the reported procedure earlier 2 ) and dry ClCH2CH2Cl (2 mL) at 60 °C. The reaction mixture was stirred at room temperature for 2 h until the reaction was complete (monitored by TLC, petroleum ether/ethyl acetate 3/1). The reaction mixture was passed over a plug of silica gel with 15 mL of CH2Cl2. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography, eluting with petroleum ether/ethyl acetate 3/1 to afford a yellow solid. Suitable crystals were obtained by slowly evaporating a mixture of hexane/dichlormethane 4/1 at room temperature.

2 Experimental details

The C-bound H atoms were geometrically placed (C–H = 0.95–0.98 Å) and refined as riding with U iso(H) = 1.2–1.5 U eq(C). The N-bound H atoms were located in a difference Fourier map but were refined with a distance restraint of N–H = 0.88 − 0.01 Å, and with U iso(H) set to 1.2 U equiv(N) 3 , 4 , 5 .

3 Comment

Fused indolines are present in a large number of biologically active alkaloids 6 . Among them, 1H-furo[3,4-b]indole is a heterocyclic compound that consists of a fused indole ring system. 1,3-Dipolar cycloaddition of carbonyl ylide and indole has been successfully applied to synthesize the key intermediate 1H-furo[3,4-b]indole 7 , 8 , 9 , 10 , 11 . It has also been identified as an important potential molecule in drug discovery due to its ability to modulate various biological targets. The unique chemical structure and diverse biological activities of 1H-furo[3,4-b]indole make it an important target for drug discovery and development. Therefore, a 1H-furo[3,4-b]indole analogue, for instance, the title compound, was synthesized.

As shown in the single crystal structure figure, there is one crystallographically independent molecule in the asymmetric unit. The compound contains two six membered rings, one aza five-membered ring and one tetrahydrofuran ring. Moreover, there are four methyl carboxylate groups. The C–O bond lengths in the carbonyl of four methyl carboxylate groups are similar. The torsion angles of C(3)–C(2)–C(7)–C(8) and C(8)–N(1)–C(3)–C(2) are 8.14(18)° and −11.88(19)° respectively, while the torsion angles of N(1)–C(8)–C(9)–O(3) and C(2)–C(7)–C(10)–O(3) are −123.58(15)° and 143.82(14)° respectively, which indicates that three fused rings are non-coplanar. In addition, the torsion angle of C(6)–C(1)–C(22)–C(23) is 42.3(3)°.


Corresponding author: Du Yuchang, College of Chemistry and Bioengineering, Yichun University, Yichun, 336000, Jiangxi, 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: Undergraduate Training Program for Innovative and Entrepreneurship in University (Grant No. 202310417006) and Research Start-Up Funding in University.

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

References

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Received: 2024-03-15
Accepted: 2024-04-30
Published Online: 2024-05-27
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.

Artikel in diesem Heft

  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
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  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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