Startseite Crystal structure and photochemical property of 1,8-bis(p-tolylthio)pyrene, C30H22S2
Artikel Open Access

Crystal structure and photochemical property of 1,8-bis(p-tolylthio)pyrene, C30H22S2

  • Wen Bin , Xu Li-Hua , Liu Na und Ni Zhong-Hai EMAIL logo
Veröffentlicht/Copyright: 22. Dezember 2018
Artikel downloaden (PDF)
Veröffentlichen auch Sie bei De Gruyter Brill
Manuskript einreichen Informationen für Autor*innen
Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 234 Heft 2

Abstract

C30H22S2, triclinic, P1̄ (no. 2), a = 7.604(4) Å, b = 11.556(5) Å, c = 13.090(7) Å, α = 93.964(8)°, β = 93.209(8)°, γ = 90.619(9)°, V = 1145.7(10) Å3, Z = 2, Rgt(F) = 0.0497, wRref(F2) = 0.1295, T = 296(2) K.

CCDC no.: 1877125

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Strip, block
Size:0.16 × 0.12 × 0.06 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.25 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:28.3°, >92% (up to 25.2, >98%)
N(hkl)measured, N(hkl)unique, Rint:7165, 5242, 0.017
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3332
N(param)refined:291
Programs:Bruker programs [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
S10.69740(9)0.43537(5)0.37831(6)0.0770(2)
S20.48251(8)−0.18943(5)0.18393(5)0.0644(2)
C10.7442(3)0.31544(18)0.45302(19)0.0594(6)
C20.7065(3)0.20003(17)0.41316(16)0.0486(5)
C30.6342(3)0.17104(18)0.31089(16)0.0527(5)
H30.61290.22990.26700.063*
C40.5965(3)0.05998(18)0.27694(16)0.0513(5)
H40.54940.04450.21020.062*
C50.6267(3)−0.03433(16)0.34018(15)0.0437(4)
C60.5844(3)−0.15114(17)0.30759(16)0.0494(5)
C70.6148(3)−0.23825(18)0.37369(18)0.0570(6)
H70.5850−0.31460.35180.068*
C80.6885(3)−0.21351(18)0.47141(18)0.0569(6)
H80.7081−0.27360.51420.068*
C90.7345(3)−0.09992(17)0.50776(15)0.0475(5)
C100.8112(3)−0.0710(2)0.60887(16)0.0591(6)
H100.8349−0.13030.65200.071*
C110.8494(3)0.0373(2)0.64281(17)0.0597(6)
H110.89960.05210.70890.072*
C120.8151(3)0.13233(19)0.58005(16)0.0525(5)
C130.8474(3)0.2477(2)0.61509(19)0.0681(7)
H130.89340.26460.68190.082*
C140.8129(3)0.3367(2)0.5533(2)0.0710(7)
H140.83580.41280.57900.085*
C150.7417(2)0.10833(16)0.47791(15)0.0444(5)
C160.7012(2)−0.00876(16)0.44145(14)0.0421(4)
C170.6594(3)−0.17370(17)0.10236(15)0.0498(5)
C180.6241(3)−0.1441(2)0.00261(18)0.0714(7)
H180.5090−0.1294−0.02000.086*
C190.7594(4)−0.1363(2)−0.06414(18)0.0756(7)
H190.7321−0.1174−0.13100.091*
C200.9313(3)−0.15558(19)−0.03429(16)0.0582(6)
C210.9657(3)−0.1832(2)0.06582(18)0.0657(6)
H211.0814−0.19590.08880.079*
C220.8326(3)−0.1925(2)0.13283(18)0.0625(6)
H220.8605−0.21180.19960.075*
C231.0778(4)−0.1467(2)−0.10675(19)0.0802(8)
H23A1.0299−0.1247−0.17190.120*
H23B1.1340−0.2204−0.11570.120*
H23C1.1627−0.0892−0.07870.120*
C240.8800(3)0.43790(17)0.29878(18)0.0591(6)
C250.8680(4)0.5036(2)0.2140(2)0.0793(8)
H250.76410.54180.19790.095*
C261.0101(5)0.5128(2)0.1532(2)0.0850(8)
H260.99910.55770.09700.102*
C271.1676(4)0.4578(2)0.1727(2)0.0762(7)
C281.1762(4)0.3923(2)0.2574(2)0.0744(7)
H281.27970.35340.27310.089*
C291.0360(3)0.3826(2)0.3194(2)0.0662(6)
H291.04740.33810.37590.079*
C301.3222(5)0.4690(3)0.1057(3)0.1110(11)
H30A1.31350.54010.07200.166*
H30B1.32100.40460.05530.166*
H30C1.43010.46950.14750.166*

Source of material

The title complex was prepared in by two steps using pyrene as the starting material. The intermediate 1,8-dibromopyrene was prepared through the bromination of pyrene according to the literature [4]. The final product was synthesized as following: 3.38 g (24 mmol) of p-methylthiophenol, 3.60 g (10 mmol) of 1,8-dibromopyrene and 50 mL of dimethylformamide were added to a 100 mL round bottom flask. The above mixture was stirred for 10 min in an ice bath under the protection of nitrogen atmosphere. Then, 0.96 g (24 mmol) of NaH (60%) was slowly added to the above flask in batches and the mixture was stirred for another 10 min. After all the generated hydrogen by the reaction was discharged, the mixture was refluxed for 10 h, poured into water, extracted with dichloromethane and washed with water for three times. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated product was purified by silica gel flash column chromatography using hexane as the eluent. Yield: 3.70 g, 86%. The light yellow strip crystals of the title compound were obtained by slow evaporation of hexane/CH2Cl2 solution (v:v = 1/1) and the selected suitable single crystal was structurally determined by X-ray diffraction analysis. Melting point: 167–170 °C. 1H NMR (400 MHz, CDCl3) δ (TMS, ppm): 8.73 (s, 2H, J = 8.73 Hz), 8.13-8.04 (m, 6H, J = 8.07 Hz), 7.23-7.20 (m, 4H), 711-7.09 (m, 4H), 2.34 (s, 6H). 13C NMR (400 MHz, CDCl3), δ (TMS, ppm): 136.72, 136.67, 133.12, 133.03, 131.61, 131.37, 131.27, 131.23, 131.15, 130.91, 130.60, 130.47, 130.25, 130.12, 130.05, 128.14, 127.63, 125.57, 125.48, 125.18, 125.03, 21.07. MALDI-TOF MS (m/z): calcd. for C30H22S2 446.1, found 446.1. Elemental analysis–calculated for C30H22S2: C, 80.68%; H, 4.96%; S, 14.36%; found: C, 80.54%, H, 4.98%; S, 14.28%.

Experimental details

All H atoms were introduced using the HFIX command in the SHELXL-2014 program [2], with the value of 0.93 Å or 0.96 Å for C—H bond distances. All H atoms were refined as riding with Uiso(H) = 1.2Ueq(C) for aromatic or Uiso(H) = 1.5Ueq(C) for methyl H atoms, respectively. The structure was checked using PLATON [5].

Comment

Up to date, a large number of new organic compounds with interesting optical, electronic, magnetic, biological and bifunctional as well as mutifunctional properties have been designed, synthesized and characterized. However, the precursors of these many organic compounds are relatively limited. Pyrene, a widely used precursor, and its derivatives have attracted considerable attention because their actual use or potential as organic light-emitting diodes (OLED), organic field effect transistor (OFET), organic lasers, chemosensors and solar cells, etc. [6], [7], [8], [9], [10], [11], [12], [13]. Among the many pyrene-based compounds, the design and synthesis of organic sulfur-containing compounds have also attracted attention because they may exhibit interesting properties originating from the their electronic structure. For instance, the introduction of a thioether group could make them useful as peroxide sensors. Up to date, there are very limited reports of the crystal structures of pyrene-based thioether compounds [14], [15], [16]. Recently, we have reported the crystal strucure of the 1,3,6,8-tetrakis(p-tolylthio)pyrene [16]. Herein, we report the synthesis, crystal structure of a new pyrene-based thioether 1,8-bis(p-tolylthio)pyrene. In addition, preliminary study indicates that the title compound could be a potential sensor for peroxides such as m-chloroperoxybenzoic acid.

In the molecular structure of the title compound, the two p-tolylthio groups are located on the same side of the pyrene ring. The main pryene core together with the two sulfur atoms are almost coplanar and the largest deviation from the main plane is 0.064(3) Å. The dihedral angle between the pyrene and two benzene rings are 85.9(3)° and 88.0(3)°, respectively. The dihedral angle between the two benzene rings is 22.6(3)°. The C—S bond distances in the title compound are very similar and distributed in a very narrow range of 1.779(2)−1.783(3) Å. The two C—S—C bond angles are very similar, with 102.77(11)° for C1—S1—C24 and 102.34(10)° for C6—S2—C17. The C—S bond distances and C—S—C bond angles are within normal ranges and comparable to those found in 1,3,6,8-tetrakis(p-tolylthio)pyrene [16]. The molecules of the title compound form a one-dimensional supramolecular structure by intermolecular π–π (pyrene) interactions. These one-dimensional supramolecular structures are linked together into three-dimensional supramolecular structure by intermolecular C—H⋯π and C—H⋯S interactions.

When the title compound was dissolved in DCM, a set of absorption peaks from 325 to 425 nm and a emission peak around 425 nm for the solution was observed. Interestingly, 1,8-bis(p-tolylthio)pyrene exhibits potential application in detection of peroxides such as m-chloroperoxybenzoic acid. The emission of 1,8-bis(p-tolylthio)pyrene in DCM is blue. When adding m-chloroperoxybenzoic acid to the DCM solution of 1,8-bis(p-tolylthio)pyrene at room temperature, the emission intensity declines drastically, as shown in Figure 1. When the molar ratio of m-chloroperoxybenzoic acid/1,8-bis(p-tolylthio)pyrene reaches 2:1, the emission is very weak. Throughout the process, the title compound displays an “on–off” optical switching property evident as an emission change from blue to colorless with the addition of m-chloroperoxybenzoic into its DCM solution. The color change is probably due to the presence of the thioether group which can be easily oxidized by m-chloroperoxybenzoic acid, yielding a sulfoxide compound which does not emit fluorescence. The present results at least indicates that the title compound could be employed as one effective sensor for the quality control or effective ingredient detection of m-chloroperoxybenzoic. More detailed investigations of the selectivity and sensitivity of this potential sensor will be carried out in the future.

Figure 1: PL spectra of 1,8-bis(p-tolylthio)pyrene in DCM in the presence of different content of m-chloroperoxybenzoic acid from 0 to 3 eq. For PL measurement, 1,8-bis(p-tolylthio)pyrene concentration: 10−5 M, excitation wavelength: 365 nm.
Figure 1:

PL spectra of 1,8-bis(p-tolylthio)pyrene in DCM in the presence of different content of m-chloroperoxybenzoic acid from 0 to 3 eq. For PL measurement, 1,8-bis(p-tolylthio)pyrene concentration: 10−5 M, excitation wavelength: 365 nm.

Acknowledgements

This work was funded by the open research fund program of Shandong Provincial Key Laboratory of Oilfield Produced Water Treatment and Environmental Pollution Control (Sinopec Petroleum Engineering Corporation).

References

1. Bruker. APEX3, SAINT-Plus, XPREP. Bruker AXS Inc., Madison, WI, USA (2016).Suche in Google Scholar

2. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Suche in Google Scholar PubMed

4. Grimshaw, J.; Trocha-Grimshaw, J.: Characterisation of 1,6- and 1,8-dibromopyrenes. J. Chem. Soc. Perkin. Trans. 1 (1972) 1622–1623.10.1039/p19720001622Suche in Google Scholar

5. Spek, A. L.: Structure validation in chemical crystallography. Acta Crystallogr. D65 (2009) 148–155.10.1107/S090744490804362XSuche in Google Scholar PubMed PubMed Central

6. Zhang, R.; Sun, H.; Zhao,Y.; Tang, X. X.; Ni, Z. H.: Dipolar 1,3,6,8-tetrasubstituted pyrene-based blue emitters containing electro-transporting benzimidazole moieties: syntheses, structures, optical properties, electrochemistry and electroluminescence. Dyes Pigm. 152 (2018) 1–13.10.1016/j.dyepig.2018.01.014Suche in Google Scholar

7. Figueira-Duarte, T. M.; Mullen, K.: Pyrene-based materials for organic electronics. Chem. Rev. 111 (2011) 7260–7314.10.1021/cr100428aSuche in Google Scholar PubMed

8. Zhang, R.; Zhao, Y.; Zhang, L. F.; Xu, L.; Ni, Z. H.: A series of short axially symmetrically 1,3,6,8-tetrasubstituted pyrene-based green and blue emitters with 4-tert-butylphenyl and aryamine attachments. Dyes Pigm. 130 (2016) 106–115.10.1016/j.dyepig.2016.03.020Suche in Google Scholar

9. Yi, J. P.; Zhao, L.; Xu, W. D.; Liu, C. F.; Lai, W. Y.; Huang, W.: Pyrene-capped starburst emitters as gain media for organic lasers: design, synthesis, and stabilized lasing properties. J. Mater. Chem. C. 4 (2016) 7546–7553.10.1039/C6TC01606ESuche in Google Scholar

10. Chu, K. H.; Zhou, Y.; Fang, Y.; Wang, L. H.; Li, J. Y.; Yao, C.: Rhodamine-pyrene conjugated chemosensors for ratiometric detection of Hg2+ ions: different sensing behavior between a spirolactone and a spirothiolactone. Dyes Pigm. 98 (2013) 339–346.10.1016/j.dyepig.2013.02.019Suche in Google Scholar

11. Liu, X.; Luo, G. P.; Cai, X. Y.; Wu, H. B.; Su, S. J.; Cao, Y.: Pyrene terminal functionalized perylene diimide as non-fullerene acceptors for bulk heterojunction solar cells. RSC Adv. 5 (2015) 83155–83163.10.1039/C5RA13188JSuche in Google Scholar

12. Liu, Y. F.; Jun, E. J.; Kim, G.; Lee, A. R.; Lee, J. H.; Yoon, J.: A bispyrene derivative as a selective fluorescent probe for RNA. Chem. Commun. 50 (2014) 2505–2507.10.1039/C3CC49430FSuche in Google Scholar PubMed

13. Gingras, M.; Placide, V.; Raimundo, J. M.; Bergamini, G.; Ceroni, P.; Balzani, V.: Polysulfurated pyrene-cored dendrimers: luminescent and electrochromic properties. Chem. Eur. J. 14 (2008) 10357–10363.10.1002/chem.200801198Suche in Google Scholar PubMed

14. Lee, S.; Chen, B. L.; Fredrickson, D. C.; DiSalvo, F. J.; Lobkovsky, E.; Adams, J. A.: Crystal structures of (pyrene)10(I3−)4(I2)10 and [1,3,6,8-tetrakis(methylthio)pyrene]3(I3−)3(I2)7: structural trends in fused aromaticpolyiodides Chem. Mater. 115 (2003) 1420–1433.10.1021/cm020651pSuche in Google Scholar

15. Oniwa, K.; Kikuchi, H.; Shimotani, H.; Ikeda, S.; Asao, N.; Yamamoto, Y.; Tanigaki, K.; Jin, T. N.: 2-Positional pyrene end-capped oligothiophenes for high performance organic field effect transistors. Chem. Commun. 52 (2016) 4800–4803.10.1039/C6CC00948DSuche in Google Scholar

16. Xu, L. H.; Ni, Z. H.: Crystal structure of 1,3,6,8-tetrakis (p-tolylthio) pyrene, C44H34S4. Z. Kristallogr. NCS 231 (2016) 255–257.10.1515/ncrs-2015-0113Suche in Google Scholar

Received: 2018-08-20
Accepted: 2018-11-05
Published Online: 2018-12-22
Published in Print: 2019-03-26

©2019 Wen Bin et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of 1H-indole-5-carboxylic acid – 4,4′-bipyridine (2/1), C14H11N2O2
  3. Crystal structure of ethyl 2-amino-4-(4-ethoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO6
  4. Crystal structure of ethyl 2-amino-4-(4-bromothiophen-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C16H16BrNO4S
  5. The crystal structure of 6-amino-2-methyl-8-(4-(methylthio)phenyl)-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile – ethanol (1/1), C20H19N5S
  6. Crystal structure of 6-amino-8-(4-isopropylphenyl)-2-methyl-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile-ethanol (1/1), C24H29N5O
  7. Crystal structure of 1,1′-(ethane-1,2-diyl)bis(3-ethyl-1H-imidazol-3-ium)bis(hexafluorido phosphate), C12H20F12N4P2
  8. Crystal structure of dimethyl (3aS,6R,6aS,7S)-2-pivaloyl-2,3-dihydro-1H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isoquinoline-3a1,6a-dicarboxylate, C21H25NO8
  9. Crystal structure of methyl 4-(4-bromothiophen-2-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H20BrNO3S
  10. Hydrothermal synthesis and crystal structure of catena-poly[bis(4-((pyridin-4-ylmethyl)amino)benzoato-κ3N:O,O′)zinc(II) – 1,2-di(pyridin-4-yl)ethene – water (1/1/1), C38H34N6O5Zn
  11. The crystal structure of 1,2-dimethyl-3,4-dinitrobenzene, C8H8N2O4
  12. Synthesis and crystal structure of trans-tetraaqua-bis(3-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)propanoato-κO)zinc(II) tetrahydrate, C38H48N2O26S2Zn
  13. Crystal structure of diaqua-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-tetrakis(chloropyridin-2-olato-κ1O)-bis(penanthroline-κ2N,N′)diterbium(III), C54H38Cl6Tb2N10O8
  14. Crystal structure of oxidobis(piperidine-1-carbodithioato-κ2S,S′)vanadium(IV), C12H20N2OS4V
  15. Crystal structure of 2-((tert-butyldimethylsilyl)oxy)-5-methylisophthalaldehyde, C15H22O3Si
  16. Crystal structure of catena-poly[tetraiodido-(μ2-1,4-bis(2-methyl-1H-imidazol-1-yl)benzene-κ2N:N′)dimercury(II)], C14H14Hg2I4N4
  17. Crystal structure of tetrakis(n-butyl)-(μ2-1,2-bis(2-oxidobenzoyl)hydrazine-1,2-diido-κ6N,O,O′:N′,O′′,O′′′)ditin(IV), C30H44N2O4Sn2
  18. Crystal structure of ethyl 2-amino-4-(4-hydroxy-3-methoxyphenyl)-7-methyl-5-oxo-4H,5H-pyrano-[4,3-b]pyran-3-carboxylate, C19H19NO7
  19. Crystal structure of 3-aminopyrazine-2-carbohydrazide, C5H7N5O
  20. Crystal structure of ethanol-bis(N-((5-(ethoxycarbonyl)-3,4-dimethyl-1H-pyrrol-2-yl)methylene)benzohydrazonato-κ2N,O)copper(II), C36H42N6O7Cu
  21. Crystal structure of 3-methyl-2-oxo-2H-chromen-7-yl propionate, C13H12O4
  22. Crystal structure of 2-(dimethylamino)ethyl 4-aminobenzoate, C11H16N2O2
  23. Crystal structure of 3-(benzo[d]thiazol-2-ylamino)isobenzofuran-1(3H)-one, C15H10N2O2S
  24. Crystal structure of 3-((1H-benzo[d]imidazol-2-yl)amino)-2-(1H-benzo[d]imidazol-2-yl)isoindolin-1-one, C22H16N6O
  25. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(4-(dimethylamino)phenyldiphenylphosphane-κP)copper(I) tetrafluoroborate, C50H48BCuF4N4P2
  26. Crystal structure of citric acid–acetonitrile (1/1), C8H11NO7
  27. Crystal structure of diethyl 2-(4-methoxyphenyl)-1-phenyl-1,2-dihydropyridine-3,5-dicarboxylate, C24H25NO5
  28. The crystal structure of poly[triaqua-bis(μ3-2,5-dihydroxyterephthalato-κ4O,O′:O′′:O′′′)-(μ4-oxalato-κ4O,O′:O′′,O′′′)cerium(III)], C9H10CeO11
  29. Crystal structure of 1-(5-(anthracen-9-yl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O2
  30. Synthesis and crystal structure of 5-(8-(((2-carboxyethyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate trihydrate, C19H23NO12S
  31. Crystal structure of rac-trans-6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromophenolato-κ4N,N′,O,O′)-bis(methanol)cobalt(III) chloride, C22H25Br2Co8N2O4Cl
  32. Crystal structure of 1-((R)-(2′-(dimethylamino)-[1,1′-binaphthalen]-2-yl))-3-((S)-2-hydroxy-1-phenylethyl)thiourea, C31H29N3OS
  33. Crystal structure and photochemical property of 1,8-bis(p-tolylthio)pyrene, C30H22S2
  34. Crystal structure of 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate, C14H18ClN5O4
  35. Crystal structure of ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate, C11H12N4O2
  36. Crystal structure of trichloro-(4-chloro-2,6-bis(diphenylmethyl)-N-((pyridin-2-yl)methylene)aniline)-aluminum dichloromethane solvate, C39H31AlCl6N2
  37. Bis(ethanol-κO)-bis(6-aminopicolinato-κ2N,O)magnesium(II), C16H22O6N4Mg
  38. Crystal structure of catena-poly[aqua-(μ2-1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ2O:O′)-(1,10-phenanthrolin-κ2N,N′)copper(II)], C16H20B10CuN2O5
  39. Crystal structure of (1,2-dicarba-closo-dodecaborane-1,2-dithiolato κ2S,S′)-bis(1,10-phenanthroline κ2N,N′)zinc(II), C26H26B10Zn4S2
  40. Crystal structure of diaqua-bis(1,10-phenanthroline-κ2N,N′)-bis(1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ3O,O′:O′′) dicobalt(II) — ethanol (1/1), C34H46B20Co2N4O11
  41. Crystal structure of ((5,5′-dimethoxy-2,2′-(1,2-phenylenebis(nitrilomethylidyne)))diphenolato-κ4O,N,O′,N′)copper(II), C22H18N2CuO4
  42. Crystal structure of 1-(5-bromo-2-(4-methoxyphenyl)-1H-indol-7-yl)ethan-1-ol, C17H14BrNO2
  43. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, C34H34N5O2Br
  44. Crystal structure of (Z)-2-((adamantan-1-ylimino)methyl)-5-methoxyphenol, C18H23NO2
  45. Crystal structure of bis((E)-2-ethoxy-6-(((2-hydroxyethyl)imino)methyl)phenolato-κ2N,O)copper(II), C22H28N2CuO6
  46. Crystal structure of 2,3-diphenyl-5,6-bis(4-methoxyphenyl)pyrazine, C30H24N2O2
  47. Crystal structure of dichlorido bis[1-((2,4-dimethyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN]cadmium(II), Cd(C12H13N5)2Cl2
  48. The crystal structure of 1,5-di(naphthalen-2-yl)-3-(pyridin-2-yl)pentane-1,5-dione, C30H23NO2
  49. The crystal structure of 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S
  50. The crystal structure of 1,4-dinitroso-2,3,5,6-tetraacetoxy-piperazine, C12H16N4O10
  51. Crystal structure of bis(2,4,6-trichlorophenyl) malonate, C15H6Cl6O4
  52. The crystal structure of trans-dichlorido-bis(pyridine-2-carboxylato-κ2N,O)platinum(IV), C12H8Cl2N2O4Pt
  53. Crystal structure of 3-nitroquinoline 1-oxide, C9H6N2O3
  54. Crystal structure of 2-(piperidin-1-ium-4-yl)-1H-benzo[d]imidazol-3-ium dichloride dihydrate, C12H21Cl2N3O2
  55. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene, C30H50O
  56. Crystal structure of (E)-4-((2-fluoro-3-(trifluoromethyl)benzylidene)amino)-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C11H8F4N4S
  57. Crystal structure of 5-(4-fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C9H8FN3S
  58. Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n
  59. The crystal structure of 4-(methoxycarbonyl)benzoic acid, C9H8O4
  60. The crystal structure of N,N′-(6-(thiophen-2-yl)-1,3,5-triazine-2,4-diyl)bis(2-methylpropane-2-sulfonamide) – ethyl acetate(2/1), C34H54N10O6S6
  61. Crystal structure of N′-(1-(2-hydroxyphenyl)ethylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide, C18H17N5O2
  62. Crystal structure of 3-(4-methoxyphenyl)-1-phenylprop-2-yn-1-one, C16H12O2
  63. Crystal structure of N′-(1-(benzofuran-2-yl)ethylidene)-2-cyanoacetohydrazide, C13H11N3O2
  64. Crystal structure of hexa-μ2-chlorido-μ4-oxido-tetrakis(1-vinyl-1H-imidazole-κN)tetracopper(II), C20H24Cu4Cl6N8O
  65. Crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide, C22H22O5N2S
  66. Crystal structure of 2-acetyl pyrene, C18H12O
https://doi.org/10.1515/ncrs-2018-0318
Creative Commons
BY 4.0

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of 1H-indole-5-carboxylic acid – 4,4′-bipyridine (2/1), C14H11N2O2
  3. Crystal structure of ethyl 2-amino-4-(4-ethoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO6
  4. Crystal structure of ethyl 2-amino-4-(4-bromothiophen-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C16H16BrNO4S
  5. The crystal structure of 6-amino-2-methyl-8-(4-(methylthio)phenyl)-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile – ethanol (1/1), C20H19N5S
  6. Crystal structure of 6-amino-8-(4-isopropylphenyl)-2-methyl-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile-ethanol (1/1), C24H29N5O
  7. Crystal structure of 1,1′-(ethane-1,2-diyl)bis(3-ethyl-1H-imidazol-3-ium)bis(hexafluorido phosphate), C12H20F12N4P2
  8. Crystal structure of dimethyl (3aS,6R,6aS,7S)-2-pivaloyl-2,3-dihydro-1H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isoquinoline-3a1,6a-dicarboxylate, C21H25NO8
  9. Crystal structure of methyl 4-(4-bromothiophen-2-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H20BrNO3S
  10. Hydrothermal synthesis and crystal structure of catena-poly[bis(4-((pyridin-4-ylmethyl)amino)benzoato-κ3N:O,O′)zinc(II) – 1,2-di(pyridin-4-yl)ethene – water (1/1/1), C38H34N6O5Zn
  11. The crystal structure of 1,2-dimethyl-3,4-dinitrobenzene, C8H8N2O4
  12. Synthesis and crystal structure of trans-tetraaqua-bis(3-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)propanoato-κO)zinc(II) tetrahydrate, C38H48N2O26S2Zn
  13. Crystal structure of diaqua-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-tetrakis(chloropyridin-2-olato-κ1O)-bis(penanthroline-κ2N,N′)diterbium(III), C54H38Cl6Tb2N10O8
  14. Crystal structure of oxidobis(piperidine-1-carbodithioato-κ2S,S′)vanadium(IV), C12H20N2OS4V
  15. Crystal structure of 2-((tert-butyldimethylsilyl)oxy)-5-methylisophthalaldehyde, C15H22O3Si
  16. Crystal structure of catena-poly[tetraiodido-(μ2-1,4-bis(2-methyl-1H-imidazol-1-yl)benzene-κ2N:N′)dimercury(II)], C14H14Hg2I4N4
  17. Crystal structure of tetrakis(n-butyl)-(μ2-1,2-bis(2-oxidobenzoyl)hydrazine-1,2-diido-κ6N,O,O′:N′,O′′,O′′′)ditin(IV), C30H44N2O4Sn2
  18. Crystal structure of ethyl 2-amino-4-(4-hydroxy-3-methoxyphenyl)-7-methyl-5-oxo-4H,5H-pyrano-[4,3-b]pyran-3-carboxylate, C19H19NO7
  19. Crystal structure of 3-aminopyrazine-2-carbohydrazide, C5H7N5O
  20. Crystal structure of ethanol-bis(N-((5-(ethoxycarbonyl)-3,4-dimethyl-1H-pyrrol-2-yl)methylene)benzohydrazonato-κ2N,O)copper(II), C36H42N6O7Cu
  21. Crystal structure of 3-methyl-2-oxo-2H-chromen-7-yl propionate, C13H12O4
  22. Crystal structure of 2-(dimethylamino)ethyl 4-aminobenzoate, C11H16N2O2
  23. Crystal structure of 3-(benzo[d]thiazol-2-ylamino)isobenzofuran-1(3H)-one, C15H10N2O2S
  24. Crystal structure of 3-((1H-benzo[d]imidazol-2-yl)amino)-2-(1H-benzo[d]imidazol-2-yl)isoindolin-1-one, C22H16N6O
  25. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(4-(dimethylamino)phenyldiphenylphosphane-κP)copper(I) tetrafluoroborate, C50H48BCuF4N4P2
  26. Crystal structure of citric acid–acetonitrile (1/1), C8H11NO7
  27. Crystal structure of diethyl 2-(4-methoxyphenyl)-1-phenyl-1,2-dihydropyridine-3,5-dicarboxylate, C24H25NO5
  28. The crystal structure of poly[triaqua-bis(μ3-2,5-dihydroxyterephthalato-κ4O,O′:O′′:O′′′)-(μ4-oxalato-κ4O,O′:O′′,O′′′)cerium(III)], C9H10CeO11
  29. Crystal structure of 1-(5-(anthracen-9-yl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O2
  30. Synthesis and crystal structure of 5-(8-(((2-carboxyethyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate trihydrate, C19H23NO12S
  31. Crystal structure of rac-trans-6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromophenolato-κ4N,N′,O,O′)-bis(methanol)cobalt(III) chloride, C22H25Br2Co8N2O4Cl
  32. Crystal structure of 1-((R)-(2′-(dimethylamino)-[1,1′-binaphthalen]-2-yl))-3-((S)-2-hydroxy-1-phenylethyl)thiourea, C31H29N3OS
  33. Crystal structure and photochemical property of 1,8-bis(p-tolylthio)pyrene, C30H22S2
  34. Crystal structure of 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate, C14H18ClN5O4
  35. Crystal structure of ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate, C11H12N4O2
  36. Crystal structure of trichloro-(4-chloro-2,6-bis(diphenylmethyl)-N-((pyridin-2-yl)methylene)aniline)-aluminum dichloromethane solvate, C39H31AlCl6N2
  37. Bis(ethanol-κO)-bis(6-aminopicolinato-κ2N,O)magnesium(II), C16H22O6N4Mg
  38. Crystal structure of catena-poly[aqua-(μ2-1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ2O:O′)-(1,10-phenanthrolin-κ2N,N′)copper(II)], C16H20B10CuN2O5
  39. Crystal structure of (1,2-dicarba-closo-dodecaborane-1,2-dithiolato κ2S,S′)-bis(1,10-phenanthroline κ2N,N′)zinc(II), C26H26B10Zn4S2
  40. Crystal structure of diaqua-bis(1,10-phenanthroline-κ2N,N′)-bis(1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ3O,O′:O′′) dicobalt(II) — ethanol (1/1), C34H46B20Co2N4O11
  41. Crystal structure of ((5,5′-dimethoxy-2,2′-(1,2-phenylenebis(nitrilomethylidyne)))diphenolato-κ4O,N,O′,N′)copper(II), C22H18N2CuO4
  42. Crystal structure of 1-(5-bromo-2-(4-methoxyphenyl)-1H-indol-7-yl)ethan-1-ol, C17H14BrNO2
  43. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, C34H34N5O2Br
  44. Crystal structure of (Z)-2-((adamantan-1-ylimino)methyl)-5-methoxyphenol, C18H23NO2
  45. Crystal structure of bis((E)-2-ethoxy-6-(((2-hydroxyethyl)imino)methyl)phenolato-κ2N,O)copper(II), C22H28N2CuO6
  46. Crystal structure of 2,3-diphenyl-5,6-bis(4-methoxyphenyl)pyrazine, C30H24N2O2
  47. Crystal structure of dichlorido bis[1-((2,4-dimethyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN]cadmium(II), Cd(C12H13N5)2Cl2
  48. The crystal structure of 1,5-di(naphthalen-2-yl)-3-(pyridin-2-yl)pentane-1,5-dione, C30H23NO2
  49. The crystal structure of 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S
  50. The crystal structure of 1,4-dinitroso-2,3,5,6-tetraacetoxy-piperazine, C12H16N4O10
  51. Crystal structure of bis(2,4,6-trichlorophenyl) malonate, C15H6Cl6O4
  52. The crystal structure of trans-dichlorido-bis(pyridine-2-carboxylato-κ2N,O)platinum(IV), C12H8Cl2N2O4Pt
  53. Crystal structure of 3-nitroquinoline 1-oxide, C9H6N2O3
  54. Crystal structure of 2-(piperidin-1-ium-4-yl)-1H-benzo[d]imidazol-3-ium dichloride dihydrate, C12H21Cl2N3O2
  55. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene, C30H50O
  56. Crystal structure of (E)-4-((2-fluoro-3-(trifluoromethyl)benzylidene)amino)-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C11H8F4N4S
  57. Crystal structure of 5-(4-fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C9H8FN3S
  58. Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n
  59. The crystal structure of 4-(methoxycarbonyl)benzoic acid, C9H8O4
  60. The crystal structure of N,N′-(6-(thiophen-2-yl)-1,3,5-triazine-2,4-diyl)bis(2-methylpropane-2-sulfonamide) – ethyl acetate(2/1), C34H54N10O6S6
  61. Crystal structure of N′-(1-(2-hydroxyphenyl)ethylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide, C18H17N5O2
  62. Crystal structure of 3-(4-methoxyphenyl)-1-phenylprop-2-yn-1-one, C16H12O2
  63. Crystal structure of N′-(1-(benzofuran-2-yl)ethylidene)-2-cyanoacetohydrazide, C13H11N3O2
  64. Crystal structure of hexa-μ2-chlorido-μ4-oxido-tetrakis(1-vinyl-1H-imidazole-κN)tetracopper(II), C20H24Cu4Cl6N8O
  65. Crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide, C22H22O5N2S
  66. Crystal structure of 2-acetyl pyrene, C18H12O
Jetzt anmelden und 20% sparen
Institutioneller Zugang
Wie funktioniert Authentifizierung?
Haben Sie eine Idee, wie wir unsere Website verbessern können?
Bitte schreiben Sie uns.
© 2025 De Gruyter Brill
Heruntergeladen am 21.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2018-0318/html
Button zum nach oben scrollen