Startseite Crystal structure of 1-methyl-3-[((naphthalen-2-ylsulfonyl)oxy)imino]indolin-2-one, C19H14N2O4S
Artikel Open Access

Crystal structure of 1-methyl-3-[((naphthalen-2-ylsulfonyl)oxy)imino]indolin-2-one, C19H14N2O4S

  • Ayman El-Faham , Sherine N. Khattab und Hazem A. Ghabbour EMAIL logo
Veröffentlicht/Copyright: 23. November 2016

Abstract

C19H14N2O4S, triclinic, P1̅, a = 5.9059(2) Å, b = 10.1508(5) Å, c = 13.6286(6) Å, α = 88.499(2)°, β = 88.744(2))°, γ = 84.569(2)°, V = 812.93(6) Å3, Z = 2, Rgt(F2) = 0.058, wR(F2) = 0.147, T = 100 K.

CCDC no.:: 1477481

The asymmetric unit of the title 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:Colourless block
Size:0.35 × 0.30 × 0.26 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:2.3 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:67.6°, >95%
N(hkl)measured, N(hkl)unique, Rint:13121, 6243, 0.041
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4320
N(param)refined:235
Programs:SHELX [17], Bruker programs [18]
Table 2

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

AtomxyzUiso*/Ueq
S10.15452(7)0.20030(4)0.79613(3)0.01541(11)
O1−0.0274(2)0.11764(12)0.80109(10)0.0226(3)
O20.3628(2)0.16299(12)0.84474(10)0.0219(3)
O30.2043(2)0.20755(12)0.67782(9)0.0167(3)
O40.7134(2)0.45030(13)0.57206(10)0.0222(3)
N10.3808(2)0.29240(14)0.65607(11)0.0155(3)
N20.7011(2)0.31287(14)0.43988(10)0.0154(3)
C10.1988(3)0.43747(16)0.87357(12)0.0132(3)
H1A0.34490.39990.89300.016*
C20.1243(3)0.57053(16)0.89564(12)0.0130(3)
C30.2626(3)0.65216(17)0.94614(13)0.0169(3)
H3A0.40890.61710.96710.020*
C40.1877(3)0.78080(18)0.96508(14)0.0214(4)
H4A0.28240.83480.99850.026*
C5−0.0300(3)0.83329(17)0.93494(14)0.0223(4)
H5A−0.08070.92280.94800.027*
C6−0.1689(3)0.75695(17)0.88712(13)0.0190(3)
H6A−0.31610.79360.86840.023*
C7−0.0960(3)0.62348(16)0.86503(12)0.0140(3)
C8−0.2327(3)0.54286(17)0.81322(13)0.0167(3)
H8A−0.37820.57900.79190.020*
C9−0.1608(3)0.41443(17)0.79308(13)0.0161(3)
H9A−0.25510.36070.75930.019*
C100.0584(3)0.36360(15)0.82406(12)0.0129(3)
C110.4488(3)0.27777(16)0.56673(12)0.0137(3)
C120.4002(3)0.19385(16)0.48641(12)0.0133(3)
C130.2421(3)0.10259(17)0.47337(13)0.0186(3)
H13A0.13370.08560.52350.022*
C140.2473(3)0.03695(17)0.38466(14)0.0205(4)
H14A0.1402−0.02510.37410.025*
C150.4061(3)0.06082(16)0.31172(13)0.0180(3)
H15A0.40570.01460.25200.022*
C160.5674(3)0.15145(16)0.32380(12)0.0163(3)
H16A0.67760.16680.27400.020*
C170.5591(3)0.21761(15)0.41145(12)0.0135(3)
C180.8651(3)0.37109(18)0.37520(13)0.0203(4)
H18A0.88460.32070.31480.030*
H18B0.81000.46300.35910.030*
H18C1.01130.36880.40810.030*
C190.6369(3)0.36072(17)0.53026(12)0.0156(3)

Source of material

3-(Hydroxyimino)-1-methylindolin-2-one was prepared first according to the reported method [1] and the spectral data was in a good agreement with the reported ones. 3-(Hydroxyimino)-1-methylindolin-2-one (1.76 g, 10 mmol) was dissolved in 20 mL dichloromethane and 10 mL of water contained NaOH (0.44 g, 11 mmol) and then naphthalene-2-sulfonyl chloride (2.49 g, 11 mmol) in 10 mL dichloromethane was added dropwise at room temperature. The reaction mixture was stirred at the same temperature for 3 h. After completion of the reaction, the organic layer was collected and the water layer was washed with 20 mL of dichloromethane. The combined organic phase was washed with H2O (20 mL), sat. solution of NaCl (20 mL), dried over MgSO4 anhydrous. After filtration the solvent was removed under reduced pressure to give the product as a brown solid. The crude product was recrystallized from dichloromethane-hexane (1:2) to give light brown crystals in 92% yield (mp 160–162 °C). 1H NMR (400 MHz, CDCl3) δ: 2.13 (s, 3H, CH3), 6.76 (d, J = 7.6 Hz, 1H, Ar), 7.09 (t, J = 8.0 Hz, 1H, Ar), 7.45 (t, J = 6.8 Hz, 1H, Ar), 7.61–7.67 (m, 2H, Ar), 7.90 (d, J = 8.0 Hz, 1H, Ar), 7.96–8.06 (m, 4H, Ar), 8.68 (s, 1H, Ar) ppm; 13C NMR (100 MHz, CDCl3) δ: 26.2, 121.2, 121.6, 127.8, 127.9, 129.5, 129.6, 129.7, 129.9, 131.2, 131.6, 131.9, 135.2, 135.6, 145.8, 149.6, 161.5 ppm. Anal. Calc. for C19H14N2O4S (366.39): C, 62.29; H, 3.85; N, 7.65; S, 8.75; found C, 62.45; H, 4.02; N, 7.58; S, 8.93.

Experimental details

Hydrogen atoms were placed in calculated positions and included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C—C bond to best fit the experimental electron density, with U(H) set to 1.5Ueq(C).

Discussion

Some isatin (indoline-2,3-dione) derivatives attracted much attention and have extensive applications as scaffold in medicinal chemistry related to their anti-bacterial, anti-virus and neuroprotection properties [2; 3; 4; 5; 6; 7; 8]. Some oxime derivatives have been also examined as useful pharmacophores in a range of therapeutic agents and considered as bioisosteres which provide a series of potent antiviral agents [9; 10; 11; 12; 13]. Recently, O-acyl and O-arylsulfonyl derivatives of isatin 3-oximes have been synthesized and their reactivity towards alcohols and amines has been reported [14; 15; 16]. O-sulfonyl derivatives were reported with better reactivity than their analogous O-acyl derivatives.

Herein we described the preparation of 1-methyl-3-[((naphthalen-2-ylsulfonyl)oxy)imino]indolin-2-one 3 from the reaction of 3-(hydroxyimino)-1-methylindolin-2-one with 4-methylbenzenesulfonyl chloride using a two-phase method (dichloromethane-water) in the presence of sodium hydroxide as base to afford the product in excellent yield and purity as observed for its spectral data.

In the crystal structure of the title compound, the unit cell contains one independent molecule. The plane of the indole ring (C11—C17/N2/C19) makes a dihedral angle with the plane of the naphthyl ring (C1—C10) of 72.56°. The molecules are packed in the crystal structure via at least two non-classical intermolecular hydrogen bonds C15—H15A⋯O2i and C18—H18C⋯O4ii. The H⋯A distances are 2.54 and 2.59 Å, respectively and the angles are 141 and 131°, respectively with symmetry code: (i) − x + 1, − y, − z + 1; (ii) − x + 2, − y + 1, − z + 1.

Acknowledgements

The authors thank the Deanship of Scientific Research at King Saud University for funding this work through Prolific Research Group Program (PRG-1437-33; Saudi Arabia).

References

1 Miao, Y.; Zhang, X.; Liu, C.; You. J.: Tris(3-hydroxyimino-1-methylindolin-2-one) monohydrate. Acta Crystallogr. E67 (2011) o1291.10.1107/S1600536811015418Suche in Google Scholar PubMed PubMed Central

2 Chen, G.; Hao, X. J.; Sun, Q. Y.; Ding, J.: Rapid eco-friendly synthesis and bioactivities of 3-nitromethylene-1,3-dihydro-indol-2-one analogues. Pap. Chem. 64 (2010) 673–677.10.2478/s11696-010-0047-1Suche in Google Scholar

3 Chen, G.; He, H. P.; Ding, J.; Hao, X.: Synthesis and antitumor activity evaluation of regioselective spiro [pyrrolidine-2,3′-oxindole] compound. J. Heterocycl. Commun. 15 (2009) 355–360.10.1515/HC.2009.15.5.355Suche in Google Scholar

4 Chen, G.; Tang, Y.; Zhang, Q. Z.;Wu, Y.; Hao, X. J.: Raoid eco-friendly and structure of 3-hydroxy-3-nitromethyl-1,3-dihydroind-2-one. J. Chem. Crystallogr. 40 (2010) 369–372.10.1007/s10870-009-9662-5Suche in Google Scholar

5 Chen, G.; Wang, Y.; Gao, S.; He, H. P.; Li, S. L.; Zhang, J. X.; Ding, J.; Hao, X. J.: Synthesis and bioactivity evaluation of 3-hydroxy-3-(phenylethynyl) indol-2-one analogues. J. Heterocycl. Chem. 46 (2009) 217–220.10.1002/jhet.58Suche in Google Scholar

6 Bramson, H. N.; Corona, J.; Davis, S. T.; Dickerson, S. H.; Edelstein, M.; Frye, S. V.; Gampe, R. T., Jr.; Harris, P. A.; Hassell, A.; Holmes, W. D.; Hunter, R. N.; Lackey, K. E.; Lovejoy, B.; Luzzio, M. J.; Montana, V.; Rocque, W. J.; Rusnak, D.; Shewchuk, L.; Veal, J. M.; Walker, D. H.; Kuyper, L. F.: Oxindole-based inhibitors of cyclin-dependent kinase 2 (CDK2): design, synthesis, enzymatic activities, and x-ray crystallographic analysis. J. Med. Chem. 44 (2001) 4339–4358.10.1021/jm010117dSuche in Google Scholar PubMed

7 Pirrung, M. C.; Pansare, S. V.; Sarma, K. D.; Keith, K. A.; Kern, E. R.: Combinatorial optimization of isatin-β-thiosemicarbazones as anti-poxvirus agents. J. Med. Chem. 48 (2005) 3045–3050.10.1021/jm049147hSuche in Google Scholar PubMed

8 Zhou, L.; Liu, Y.; Zhang, W.; Wei, P.; Huang, C.; Pei, J.; Yuan, Y.; Lai, L.: Isatin compounds as noncovalent SARS coronavirus 3C-like protease inhibitors. J. Med. Chem. 49 (2006) 3440–3443.10.1021/jm0602357Suche in Google Scholar PubMed

9 Combrink, K. D.; Gulgeze, H. B.; Thuring, J. W.; Yu, K.-L.; Civiello, R. L.; Zhang, Y.; Pearce, B. C.; Yin, Z.; Langley, D. R.; Kadow, K. F.; Cianci, C. W.; Li, Z.; Clarke, J.; Genovesi, E. V.; Medina, I.; Lamb, L.; Yang, Z.; Zadjura, L.; Krystal, M.; Meanwell, N. A.: Respiratory syncytial virus fusion inhibitors. Part 6: An examination of the effect of structural variation of the benzimidazol-2-one heterocycle moiety. Bioorg. Med. Chem. Lett. 17 (2007) 4784–4790.10.1016/j.bmcl.2007.06.065Suche in Google Scholar PubMed

10 Wang, X. A.; Cianci, C. W.; Yu, K.-L.; Combrink, K. D.; Thuring, J. W.; Zhang, Y.; Civiello, R. L.; Kadow, K. F.; Roach, J.; Li, Z.; Lanley, D. R.; Krystal, M.; Meanwell, N. A.: Respiratory syncytial virus fusion inhibitors. Part 5: Optimization of benzimidazole substitution patterns towards derivatives with improved activity. Bioorg. Med. Chem. Lett. 17 (2007) 4592–4598.10.1016/j.bmcl.2007.05.102Suche in Google Scholar PubMed

11 Yu, K.-L.; Sin, N.; Civiello, R. L.; Wang, X. A.; Combrink, K. D.; Gulgeze, H. B.; Venables, B. L.; Wright, J. J. K.; Dalterio, R. A.; Zadjura, L.; Marino, A.; Dando, S.; D’Arienzo, C.; Kadow, K. F.; Cianci, C. W.; Li, Z.; Clarke, J.; Genovesi, E. V.; Medina, I.; Lamb, L.; Colonno, R. J.; Yang, Z.; Krystal, M.; Meanwell, N. A.: Respiratory syncytial virus fusion inhibitors. Part 4: Optimization for oral bioavailability. Bioorg. Med. Chem. Lett. 17 (2007) 895–901.10.1016/j.bmcl.2006.11.063Suche in Google Scholar PubMed

12 Han, H. O.; Kim, S. H.; Kim, K.-H.; Hur, G.-C.; Yim, H. J.; Chung, H.-K.; Woo, S. H.; Koo, K. D.; Lee, C.-S.; Koh, J. S.; Kim, G. T.: Design and synthesis of oxime ethers of α-acyl-β-phenylpropanoic acids as PPAR dual agonists. Bioorg. Med. Chem. Lett. 17 (2007) 937–941.10.1016/j.bmcl.2006.11.050Suche in Google Scholar PubMed

13 Huang, S.; Li, R.; Connolly, P. J.; Xu, G.; Gaul, M. D.; Emanuel, S. L.; LaMontagne, K. R.; Greenberger, L. M.: Synthesis and biological study of 4-aminopyrimidine-5-carboxaldehyde oximes as antiproliferative VEGFR-2 inhibitors. Bioorg. Med. Chem. Lett. 16 (2006) 6063–6066.10.1016/j.bmcl.2006.08.107Suche in Google Scholar PubMed

14 Stankevicius, A. P.; Terentiev, P. B.; Janushene, L. N.; Savickas, A. B.: Acylating and arylsulfonylating ability of O-derivatives of isatin 3-oximes. Chem. Heterocycl. Compd. 41 (2005) 98–104.10.1007/s10593-005-0114-7Suche in Google Scholar

15 Stankevicius, P.; Terentiev, P. B.; Janushene, L. N.; Vainauskas. P. V.: Cleavage of O-acylates of isatin 3-oximes in the presence of alcohols. Chem. Heterocycl. Compd. 39 (2003) 1523–1524.10.1023/B:COHC.0000014419.10175.afSuche in Google Scholar

16 El-Faham, A.; Elnakdy, Y. A.; El Gazzar, S. A. M.; El-Rahman, M. M. A.; Sh. N. Khattab.: Synthesis, characterization and anti-proliferation activities of novel cyano oximino sulfonate esters. Chem. Pharm. Bull. 62 (2014) 373–378.10.1248/cpb.c13-01005Suche in Google Scholar PubMed

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

18 Bruker. APEX2, SAINT and SADABS. Brucker AXS Inc., Madison, Wisconsin, USA, 2009.Suche in Google Scholar

Received: 2016-7-9
Accepted: 2016-10-28
Published Online: 2016-11-23
Published in Print: 2017-1-1

©2016 Ayman El-Faham et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Editorial
  3. Twenty years of crystal structure publication and the road ahead
  4. Crystal Structures
  5. Crystal structure of poly-[triaqua-(μ4-5′-carboxy-[1,1′-biphenyl]-2,3,3′-tricarboxylate-κ6O1,O2:O3,O4:O5:O6)praseodymium(III), C16H13O11Pr
  6. Crystal structure of (R)-1-(2,3-dihydro-1H-pyrrolizin-5-yl)-2,3-dihydroxypropan-1-one, C10H13NO3
  7. Crystal structure of (E)-4-nitro-2-((2-phenoxyphenylimino)methyl)phenol, C19H14N2O4
  8. Crystal structure of 3,3′-di(furan-2-yl)-5,5′-bi-1,2,4-triazine
  9. Crystal structure of 11-(p-coumaroyloxy)-tremetone, C22H20O5
  10. The crystal structure of 1,3-bis(2,6-diiso-propylphenyl)imidazol-2-ylidene)-dibromido-(1-methyl-1H-imidazole-κ1N)palladium(II) – ethyl acetate – water (1/1/1), C31H42Br2N4Pd
  11. Crystal structure of 2-((3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-1H-indene-1,3(2H)-dione, C28H19N5O2
  12. Crystal structure of 2-(5-(4-fluorophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)-4-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)thiazole, C29H25FN6S
  13. Crystal structure of poly-[aqua-(μ7-benzene-1,3,5-tricarboxylato)-(μ3-1,2,4-triazol-1-ido)dicobalt(II)], C11H7Co2N3O7
  14. Crystal constructure of 16(S)-methyl-6α-carboxy-1, 15-dioxo-6, 7-seco-ent-kaur-2-en-7, 20-olide, C20H24O6
  15. Crystal structure of 1-(benzo[d]thiazol-2-yl)-3-phenylthiourea, C14H11N3S2
  16. Crystal structure of 3-(2-bromophenyl)-1,1-dimethylthiourea, C9H11BrN2S
  17. Crystal structure of 1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea, C17H21ClN2S
  18. Crystal structure of 3-(adamantan-1-yl)-1-(4-bromophenyl)urea, C17H21BrN2O
  19. Crystal structure of (Z)-Ethyl 2-cyano-2-(3-phenylthiazolidin-2-ylidene) acetate, C14H14N2O2S
  20. Crystal structure of methyl 2b-ethyl-1a,2a,2b,2b1,3,5,10,11-octahydro-1H-oxireno[2′,3′:6,7]indolizino[8,1-cd]carbazole-4-carboxylate, C21H24N2O3
  21. Crystal structure of 2-amino-5-oxo-4-(3,4,5-trimethoxy-phenyl)-4,5,6,7-tetrahydro-cyclopenta[b]pyran-3-carbonitrile, C18H18N2O5
  22. Crystal structure of 1,2,3-trimethyl-2,3-dihydro-1H-perimidine, C14H16N2
  23. Crystal structure of bis(2,6-dihydroxymethyl)pyridine-κ3N,O,O′)-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-bis(6-chloropyridin-2-olato-κO)-bis(nitrato-κ2O,O′)digadolinium(III), C34H30Cl4Gd2N8O14
  24. Crystal structure of 8-isopropyl-8-aza-bicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate, C19H27NO3
  25. Crystal structure of 1-methyl-3-[((naphthalen-2-ylsulfonyl)oxy)imino]indolin-2-one, C19H14N2O4S
  26. Crystal structure (7,8-bis(diisopropylphosphino)-7,8-dicarba-nido-undecaborane-κ2P,P′)-(benzoato-κ2O,O′)nickel(II), C21H42B9NiO2P2
  27. Crystal structure of methyl-2-methyl-4-(2-oxo-2-phenylethyl)-5-phenyl-1H-pyrrole-3-carboxylate, C21H19NO3
  28. Crystal structure of 2-[(2-oxo-thiazolidine-3-carbonyl)sulfamoyl]-methy-benzoic acid methyl ester, C13H14N2O6S2
  29. Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C13H14N2O3S
  30. Crystal structure of 1,1′-(hexane-1,6-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(hexafluoro phosphate), C14H24F12N4P2
  31. Crystal structure of di-μ-chlorido-bis[1,2-bis(dicyclohexylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]zinc(II), C52H108B20Cl2P4Zn2
  32. Crystal structure of dibromido-bis[μ-1-[(2-methyl-1H-benzoimidazol-1-yl)methyl]-1H-benzotriazole-κN]mercury(II), C30H26Br2HgN10
  33. Crystal structure of bis(μ-nitrato-κ2O:O)-bis[1,2-bis(diphenylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]disilver(I) dicloromethane monosolvate, C54H64B20Cl4O6P4Ag2
  34. Crystal structure of dinuclear dichloridobis(dimethylformamide-kO)bis[μ2-3-(2-oxyphenyl)-5-(pyrazin-2-yl)-1,2,4-triazol-1ido-κ4-O,N:N′,N′′(2)]diiron(III) dimethylformamide (1/1), C36H42Cl2Fe2N14O6
  35. Crystal structure of diaqua-dinitrato-κO-bis(4-(1H-pyrazol-3-yl)pyridine-κN)manganese(II), C16H18MnN8O8
  36. Crystal structure of (Z)-6-methoxy-2-(2,2,2-trifluoro-1-hydroxyethylidene)-2,3-dihydro-1H-inden-1-one, C12H6F6O3
  37. Crystal Structure of 4-(2-chloroacetamido)pyridinium chloride monohydrate, C7H10Cl2N2O2
  38. Crystal structure of 2-amino-4-(4-chloro-phenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H13ClN2O2
  39. Crystal structure of (E)-1-(2-(thiophen-2-ylmethylene)hydrazinyl)phthalazine hydrochloride–ethanol (1/1), C15H17ClN4OS
  40. Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C9H12BrN3O3
  41. Crystal structure of 3-(2-(4-chlorophenyl)-3-hydroxy-3,3-diphenylpropyl)-1,1-dimethylurea, C24H25ClN2O2
  42. Crystal structure of 3-(4-chlorophenyl)-1,1-dimethylthiourea, C9H11ClN2S
  43. Crystal structure of 2-amino-4-(4-bromo-phenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C16H11BrN2O3
  44. Crystal structure of 4-(3,4-dimethyl-phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester, C21H25NO3
  45. Crystal structure of (E)-2-({4-hydroxy-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]phenyl} methylidene)-1-indanone, C23H26N2O3
  46. Crystal structure of tripropylammonium 2′-carboxy-[1,1′-biphenyl]-2-carboxylate – [1,1′-biphenyl]-2,2′-dicarboxylic acid (2/1), C60H72N2O12
  47. Crystal structure of catena-poly-{aqua-[μ2-1,2-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′]-[μ2-4,4′-(dimethylsilanediyl)dibenzato-κ3O,O′:O′]nickel(II)}, C30H30N4NiO5Si
  48. The crystal structure of 1-(4-bromophenyl)-2-(4-(4-fluorophenyl)piperazin-1-yl)ethanol, C18H20BrFN2O1
  49. Crystal structure of trimethylammonium 4-((4-carboxyphenyl)sulfonyl)benzoate, C17H19NO6S
  50. Crystal structure of syn-2,4-di-o-tolylpentane-2,4-diol, C19H24O2
  51. Crystal structure of 2-[3,5-bis(trifluoromethyl)benzylsulfanyl]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C15H7BrF6N2OS2
  52. Crystal structure of (E)-3-((naphthalen-1-ylimino)methyl)-4-nitrophenol, C17H12N2O3
  53. Crystal structure of 2-dichloromethyl-2-p-nitrophenyl-1,3-dioxolane, C10H9Cl2NO4
  54. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanopalladate(II), C14H24N8Pd2
  55. Crystal structure of 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic acid monohydrate, C5H7NO4S2
  56. Crystal structure of a P4-bridged (η5-pentamethyl-cyclopentadienyl)(η5-adamantylcyclopentadienyl) titanium(III)complex, C50H66P4Ti2
  57. Crystal structure of cis-bis(2,2′-bipyrimidine-κ2N,N′)bis(thiocyanato-κN)nickel(II), C18H12N10NiS2
  58. Crystal structure of cis-bis(2,2′-bipyridine-κ2N,N′)dibromidomanganese(II), C20H16Br2MnN4
  59. Crystal structure of cis-bis(2,2′-bipyridine-κ2N,N′)bis(thiocyanato-κN)nickel(II), C22H16N6NiS2
  60. Crystal structure of trans-dibromido(1,4,8,11-tetraazacyclotetradecane)nickel(II), C10H24Br2N4Ni
  61. Crystal structure of cis-tetrabromidobis(pyridine-κN)platinum(IV), C10H10Br4N2Pt
  62. Crystal structure of (E)-5-((4-chlorophenyl)diazenyl)-2-(5-(4-fluorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole, C23H17ClFN5S2
  63. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridocobaltate(II) monohydrate, C10H18Cl4CoN2O
Heruntergeladen am 5.10.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2016-0146/html
Button zum nach oben scrollen