Startseite Crystal structure of dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-5,10-dione, C14H4O2S4
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Crystal structure of dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-5,10-dione, C14H4O2S4

  • Yan Jia , Pengling Yu , Shihui Li , Yumei Zhao und Xiaoxin Zheng ORCID logo EMAIL logo
Veröffentlicht/Copyright: 12. Mai 2023

Abstract

C14H4O2S4, monoclinic, P21/n (no. 14), a = 3.85180(10) Å, b = 8.9728(2) Å, c = 18.0073(4) Å, β = 93.554(1)°, V = 621.16(3) Å3, Z = 2, R gt (F) = 0.0411, wR ref (F 2) = 0.1091, T = 301(2) K.

CCDC no.: 2257052

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: Brown plate
Size: 0.11 × 0.10 × 0.03 mm
Wavelength: CuKα radiation (1.54178 Å)
μ: 7.00 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 68.2°, 97 %
N(hkl)measured, N(hkl)unique, R int: 7812, 1113, 0.060
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 989
N(param)refined: 91
Programs: Bruker [1], SHELX [2, 3]
Table 2:

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

Atom x y z U iso*/U eq
S1 0.5683 (2) 0.22415 (9) 0.29064 (4) 0.0325 (3)
S2 0.2353 (2) 0.32906 (9) 0.49968 (4) 0.0311 (3)
O1 0.7439 (7) −0.1004 (3) 0.37078 (13) 0.0454 (6)
C1 0.4279 (8) 0.4063 (4) 0.28831 (18) 0.0352 (7)
H1 0.433315 0.465748 0.246101 0.042*
C2 0.4675 (7) 0.2088 (3) 0.38217 (17) 0.0272 (6)
C3 0.4935 (7) 0.0967 (3) 0.43687 (16) 0.0266 (6)
C4 0.3738 (8) 0.1465 (4) 0.50361 (17) 0.0294 (7)
C5 0.6317 (8) −0.0560 (4) 0.42909 (17) 0.0288 (7)
C6 0.3088 (8) 0.4557 (4) 0.35309 (18) 0.0335 (7)
H2 0.223467 0.551062 0.360701 0.040*
C7 0.3324 (7) 0.3421 (4) 0.40749 (17) 0.0282 (7)

1 Source of materials

1.12 g (5.3 mmol) of N,N-dimethylthieno[3,2-b]thiophene-3-carboxamide was added to 30 mL of dried THF in a flask under N2 atmosphere. After the solution was cooled to 273 K, n–BuLi (1.6 M in n-hexane, 3.6 ml, 1.1 eq.) was added dropwise during 30 min. The mixture was then stirred at room temperature for 30 min. Next, it was poured into the ice/water mixture (5 g) and stirred for 3 h. Finally, the mixture was filtered and the brown precipitate washed with water (100 mL), methanol (30 mL), and THF (30 mL). The dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-5,10-dione was obtained as a brown powder (0.71 g, 81 %) after drying in a vacuum desiccator.

2 Experimental details

All hydrogen atoms were placed in idealized positions. Their U iso values were set to 1.2U eq of the parent atoms.

3 Comment

The dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-5,10-dione has been established to be a widely used intermediate for highly efficient solar cell materials [45]. Therefore, the analyzation and development of its analogs and derivatives are of increasing interest to academics.

The crystal structure of dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-5,10-dione is shown in the figure. The title molecule is located around an inversion centre. The bond lengths of C5=O1 in the title molecule is 1.226 Å, which is similar to those reported in the literature [6, 7]. Besides, all the atoms are in the same plane, and the distance between two adjacent molecules in parallel arrangement is 3.478 Å, shorter than 3.800 Å, indicating possible ππ stacking interaction between planar unsaturated cycles. The bond lengths and angles are all in the expected ranges.


Corresponding author: Xiaoxin Zheng, State Key Laboratory of Crystal Materials, Shandong University, Jinan, 250100, P.R. 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

1. Bruker. SAINT, APEX2 and SADABS; Bruker AXS Inc.: Madison, WI, 2012.Suche in Google Scholar

2. Sheldrick, G. M. SHELXTL – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Suche in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Suche in Google Scholar

4. Zhang, L., Zhu, X., Deng, D., Wang, Z., Zhang, Z., Li, Y., Zhang, J., Lv, K., Liu, L., Zhang, X., Zhou, H., Ade, H., Wei, Z. High miscibility compatible with ordered molecular packing enables an excellent efficiency of 16.2% in all-small-molecule organic solar cells. Adv. Mater. 2022, 34, e2106316.10.1002/adma.202106316Suche in Google Scholar PubMed

5. Huang, J., Peng, R., Xie, L., Song, W., Hong, L., Chen, S., Wei, Q., Ge, Z. A novel polymer donor based on dithieno[2,3-d:2′,3′-d″]benzo[1,2-b:4,5-b′]dithiophene for highly efficient polymer solar cells. J. Mater. Chem. A 2019, 7, 2646–2652; https://doi.org/10.1039/c8ta11004b.Suche in Google Scholar

6. Li, C. Crystal structure of 2-(tert-pentyl)anthracene-9,10-dione, C19H18O2. Z. Kristallogr. N. Cryst. Struct. 2022, 237, 917–919; https://doi.org/10.1515/ncrs-2022-0330.Suche in Google Scholar

7. Rather, S. A., Saha, B. K. Understanding the elastic bending mechanism in a 9,10-anthraquinone crystal through thermal expansion study. CrystEngComm 2021, 23, 5768–5773; https://doi.org/10.1039/d1ce00467k.Suche in Google Scholar

Received: 2023-04-18
Accepted: 2023-04-29
Published Online: 2023-05-12
Published in Print: 2023-08-28

© 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
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  4. The crystal structure of (1E,2E)-1,2-bis(quinolin-2-ylmethylene)hydrazine, C20H14N4
  5. 5-Amino-2-chloro-4-fluoro-N-(N-isopropyl-N-methylsulfamoyl) benzamide, C11H15O3ClFN3S
  6. Crystal structure of trans-N 1,N 8-bis(2-cyanoethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H42N6
  7. The crystal structure of [N-{[2-(oxy)-4-methoxyphenyl](phenyl)methylidene}alaninato]-diphenyl-silicon(IV) – chloroform (1/1), C29H25NO4Si·CHCl3
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  9. Crystal structure of baryte from Mine du Pradet (France)
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  12. The crystal structure of diaqua-methanol-κ1 O- (3-thiophenecarboxylato-κO)-(2,2′-dipyridyl-κ2 N,N′)manganese(II) 3-thiophenecarboxylate, C21H22N2O7S2Mn
  13. Crystal structure of catena-poly[tetrakis(butyl)-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O:O,O′,N-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O,N,O′:N′-ditin(IV)], C34H50N6O6Sn2
  14. Crystal structure of 4-chloro-N′-[(1E)-(2-nitrophenyl)methylidene]benzohydrazide, C14H10ClN3O3
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  16. The crystal structure of (Z)-4-amino-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H17N3O
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  19. The crystal structure of catena-poly[bis(1-ethylimidazole-k1 N)-(μ 2-benzene-1-carboxyl-3,5-dicarboxylato-κ 2 O, O′)zinc(II)], C19H20N4O6Zn
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  23. Crystal structure of 3,5–di-O-benzoyl-1,2-O-isopropylidene-α–D-ribose, C22H22O7
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  25. The crystal structure of (E)-N′-(4-hydroxy-3-methoxybenzylidene)-2-naphthohydrazide monohydrate, C19H18N2O4
  26. The crystal structure of 5,5′-diselanediyl-bis(2-hydroxybenzaldehyde), C14H10O4Se2
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