Startseite 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
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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

  • Ming Ni und Penghui Ni ORCID logo EMAIL logo
Veröffentlicht/Copyright: 23. März 2023

Abstract

C22H22N2O2S4, triclinic, P 1 (no. 2), a = 8.4865(14) Å, b = 11.756(2) Å, c = 12.863(2) Å, α = 69.693(2)°, β = 70.812(2)°, γ = 72.170(2)°, V = 1109.6(3) Å3, Z = 2, Rgt (F) = 0.0280, wRref (F 2) = 0.0753, T = 296(2) K.

CCDC no.: 2243750

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 block
Size: 0.24 × 0.20 × 0.18 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.45 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 25.1°, 99%
N(hkl)measured, N(hkl)unique, R int: 5747, 3909, 0.012
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3598
N(param)refined: 274
Programs: Bruker [1], SHELX [2, 3], WinGX/ORTEP [4]
Table 2:

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

Atom x y z U iso*/U eq
S1 0.30505 (5) 0.43595 (4) 0.05875 (3) 0.03909 (13)
S2 0.08586 (6) 0.36363 (4) 0.13404 (4) 0.04479 (14)
S3 −0.09841 (6) 0.49793 (4) 0.19691 (4) 0.04544 (14)
S4 −0.04806 (5) 0.49521 (4) 0.34560 (4) 0.04032 (13)
N1 0.52786 (16) 0.28226 (12) 0.19098 (11) 0.0328 (3)
N2 0.02421 (16) 0.72373 (12) 0.29725 (11) 0.0320 (3)
O1 0.88268 (16) 0.14416 (13) 0.08488 (10) 0.0517 (3)
O2 −0.14690 (17) 0.86798 (12) 0.46899 (11) 0.0512 (3)
C1 0.40182 (19) 0.39113 (14) 0.17194 (13) 0.0299 (3)
C2 0.37975 (18) 0.45613 (13) 0.24871 (13) 0.0282 (3)
C3 0.49745 (18) 0.38488 (13) 0.31816 (13) 0.0289 (3)
C4 0.5275 (2) 0.40060 (16) 0.41285 (14) 0.0381 (4)
H4 0.468197 0.470160 0.439187 0.046*
C5 0.6463 (2) 0.31108 (18) 0.46597 (16) 0.0465 (4)
H5 0.667655 0.320343 0.528705 0.056*
C6 0.7357 (2) 0.20591 (18) 0.42634 (16) 0.0494 (5)
H6 0.816184 0.147208 0.463225 0.059*
C7 0.7079 (2) 0.18704 (16) 0.33464 (16) 0.0434 (4)
H7 0.767099 0.116699 0.309526 0.052*
C8 0.58685 (19) 0.27800 (14) 0.28061 (13) 0.0317 (3)
C9 0.5777 (2) 0.18468 (15) 0.13328 (16) 0.0423 (4)
H9A 0.484888 0.190437 0.102136 0.051*
H9B 0.592905 0.104685 0.189665 0.051*
C10 0.7385 (2) 0.18906 (17) 0.03817 (15) 0.0479 (5)
H10A 0.745251 0.138493 −0.009454 0.057*
H10B 0.736857 0.273842 −0.009285 0.057*
C11 1.0371 (3) 0.1533 (2) −0.00127 (18) 0.0589 (5)
H11A 1.050788 0.104364 −0.051121 0.088*
H11B 1.131502 0.123162 0.033640 0.088*
H11C 1.033589 0.238548 −0.044717 0.088*
C12 0.08661 (19) 0.59964 (14) 0.29602 (13) 0.0302 (3)
C13 0.26297 (19) 0.57474 (13) 0.25999 (12) 0.0283 (3)
C14 0.31247 (19) 0.68843 (13) 0.23922 (12) 0.0280 (3)
C15 0.4707(2) 0.72321 (16) 0.19720 (14) 0.0368 (4)
H15 0.571531 0.665444 0.180230 0.044*
C16 0.4739 (2) 0.84446 (17) 0.18159 (16) 0.0465 (4)
H16 0.577949 0.868785 0.153388 0.056*
C17 0.3219 (2) 0.93216 (17) 0.20771 (17) 0.0467 (4)
H17 0.328003 1.013224 0.197145 0.056*
C18 0.1652 (2) 0.90148 (15) 0.24827 (15) 0.0393 (4)
H18 0.065411 0.960070 0.265174 0.047*
C19 0.16130 (19) 0.77873 (14) 0.26325 (13) 0.0291 (3)
C20 −0.1553 (2) 0.78774 (16) 0.32461(15) 0.0398 (4)
H20A −0.223086 0.746628 0.307457 0.048*
H20B −0.167379 0.872246 0.275507 0.048*
C21 −0.2260 (2) 0.79165 (17) 0.44748 (16) 0.0469 (4)
H21A −0.348532 0.824304 0.462347 0.056*
H21B −0.204899 0.708319 0.497967 0.056*
C22 −0.2125 (3) 0.8773 (2) 0.58304 (18) 0.0694 (6)
H22A −0.330950 0.918527 0.594549 0.104*
H22B −0.149746 0.924073 0.596502 0.104*
H22C −0.201041 0.795560 0.635280 0.104*

Source of material

All chemicals were purchased from commercial sources and used as received without further purification. A mixture of 17.5 g of 1-(2-methoxyethyl)-1H-indole, 9.6 g of sulfur and 60 ml of N,N-dimethylformamide was stirred under nitrogen in an oil-bath maintained at 150 °C for 6 h, and then allowed to cool slowly overnight in the oil-bath. The yellow crystals which appeared were removed and thoroughly washed with carbon disulfide. The yield of pure 5,10-bis(2-methoxyethyl)-5,10-dihydro-[1,2,3,4]tetrathiocino[5,6-b:8, 7-b′]diindole, was 11.1 g (47%). Subsequently, dissolve 1 g of the target compound in 30 ml of dichloromethane, heat reflux until the solid is completely dissolved, filtered. Finally, the title crystal was precipitated by controlling solvent volatilization.

Experimental details

All H-atoms bonded to C atoms were placed geometrically and refined using a riding model with common isotropic displacement factors U iso(H) = 1.2 or 1.5 U eq (parent C-atom).

Comment

As a special class of sulfur-rich compounds, polysulfide heterocyclic compounds show important biologically active functions and have great potential in the treatment of major diseases such as cancer and HIV [5, 6]. However, it is difficult to characterize the structure of compounds. So, the synthesis and crystal structure of the title compound are of great significance to studying the application.

Single-crystal structure analysis revealed that the title compound crystallized in the triclinic space group P 1 . The Ortep diagram is presented in Figure 1. The bond lengths of S–S in the title molecule is 2.0335(7)–2.0817(7) Å, it is similar to reported in the literature [7], [8], [9], [10]. The bond lengths of C1–S1 and C12–S4 in the title molecule are 1.7494(16) and 1.7483(15) Å, respectively. They are similar to reported in the literature [11], [12], [13], [14].


Corresponding author: Penghui Ni, School of Chemistry and Materials Science, Key Laboratory of Functional Metal–Organic Compounds of Hunan Province, Hengyang Normal University, Hengyang, Hunan 421008, China, E-mail:

Funding source: Scientific & Technological Projects of Hengyang City

Award Identifier / Grant number: 202150063426

Award Identifier / Grant number: 21B0634

Funding source: Science Foundation of Hengyang Normal University of China

Award Identifier / Grant number: 2020QD07

Funding source: Key Laboratory of Functional Metal–Organic Compounds of Hunan Province

Award Identifier / Grant number: 2022HSKFJJ024

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

  2. Research funding: This work was supported by the Scientific & Technological Projects of Hengyang City (No. 202150063426), Scientific Research Fund of Hunan Provincial Education Department of China (No. 21B0634), Science Foundation of Hengyang Normal University of China (No. 2020QD07) and Key Laboratory of Functional Metal–Organic Compounds of Hunan Province (2022HSKFJJ024).

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

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Received: 2023-02-21
Accepted: 2023-03-09
Published Online: 2023-03-23
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
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  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
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  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
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  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,,]chloridopalladium(II) chloride monohydrate
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  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
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  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
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