Startseite The crystal structure of 4-tert-butyl-N′-[(E)-(4-fluoro-3-methoxyphenyl)methylidene]benzohydrazide, C19H21F1N2O2
Artikel Open Access

The crystal structure of 4-tert-butyl-N′-[(E)-(4-fluoro-3-methoxyphenyl)methylidene]benzohydrazide, C19H21F1N2O2

  • Muhammad Ikram , Momin Khan , Sajjad Ahmad , Sadia Rehman und Carola Schulzke EMAIL logo
Veröffentlicht/Copyright: 3. Mai 2018

Abstract

C19H21F1N2O2, monoclinic, Cc (no. 9), a = 14.337(3) Å, b = 15.549(3) Å, c = 8.0212(16) Å, β = 103.33(3)°, V = 1740.0(6) Å3, Z = 4, Rgt(F) = 0.0796, wRref(F2) = 0.2192, T = 170 K.

CCDC no.: 1561397

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:Needle, colorless
Size:0.48 × 0.20 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:STOE IPDS2T, ω-scans
θmax, completeness:26.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:7545, 3151, 0.071
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2812
N(param)refined:226
Programs:Stoe programs [1], SHELX [2, 3] , WinGX and ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
C10.9240(5)0.7308(6)0.9799(13)0.091(3)
H1A0.9855780.7388141.0621020.136*
H1B0.8797130.7765630.9950820.136*
H1C0.9338900.7331000.8630410.136*
C20.9529(5)0.5718(7)1.0029(13)0.098(3)
H2A1.0066690.5754381.1033040.146*
H2B0.9768110.5777500.8984200.146*
H2C0.9209830.5160361.0021650.146*
C30.8625(5)0.6429(5)1.1890(9)0.0689(19)
H3A0.8350210.5873411.2098160.103*
H3B0.8173110.6890011.1981290.103*
H3C0.9227220.6520611.2741920.103*
C40.8819(4)0.6435(4)1.0101(9)0.0603(17)
C50.7909(3)0.6276(3)0.8682(7)0.0414(11)
C60.7009(3)0.6228(3)0.9027(7)0.0393(10)
H60.6938290.6325161.0160380.047*
C70.6207(3)0.6039(3)0.7739(6)0.0347(9)
H70.5594190.6011570.8002390.042*
C80.6287(3)0.5890(3)0.6087(6)0.0318(9)
C90.7179(3)0.5973(3)0.5702(7)0.0394(10)
H90.7244070.5897740.4558210.047*
C100.7977(3)0.6165(4)0.7000(7)0.0458(12)
H100.8584480.6221870.6726880.055*
C110.5460(3)0.5624(3)0.4677(6)0.0306(8)
C120.3670(3)0.4107(3)0.4470(6)0.0356(9)
H120.3885830.3912570.5616930.043*
C130.2837(3)0.3689(3)0.3344(6)0.0361(10)
C140.2311(3)0.3106(3)0.4051(7)0.0452(11)
H140.2501880.2966370.5233610.054*
C150.1495(4)0.2723(4)0.3022(8)0.0510(13)
H150.1129600.2319710.3493420.061*
C160.1236(3)0.2940(3)0.1328(8)0.0483(13)
C170.1762(3)0.3501(4)0.0563(7)0.0457(11)
C180.2572(3)0.3886(3)0.1600(7)0.0400(10)
H180.2942640.4280450.1118700.048*
C190.1951(6)0.4235(8)−0.1910(10)0.095(3)
H19A0.1858610.481102−0.1477800.143*
H19B0.1711740.422434−0.3157510.143*
H19C0.2634670.409166−0.1620690.143*
N10.4862(2)0.5059(2)0.5160(5)0.0320(8)
N20.4107(2)0.4723(2)0.3936(4)0.0320(8)
O10.5367(2)0.5880(2)0.3196(4)0.0376(7)
O20.1439(3)0.3625(3)−0.1149(6)0.0632(12)
F10.0448(2)0.2578(2)0.0320(5)0.0654(10)
H1N0.502(4)0.479(3)0.623(7)0.031(12)*

Source of materials

The title compound 4-tert-butyl-N′-[(E)-(4-fluoro-3-methoxyphenyl)methylidene] benzohydrazide was synthesized by condensing 1 mmol of 4-tert-butyl benzohydrazide with 1 mmol of 4-fluoro-3-methoxybenzaldehyde. Both reactants were dissolved in minimum amount of distilled and dried ethanol before mixing. A catalytic amount of acetic acid was added to the reaction mixture and the resulting mixture was refluxed for about 5 h. During the synthetic process the reaction progress was monitored by TLC. After completion of the reaction the reaction mixture was allowed to cool to room temperature. Transparent crystals were isolated from the solution by allowing it to stand for 6–12 h.

Experimental details

The absolute structure could not be determined crystallographically beyond doubt (non-centrosymmetric space group; the molecule itself does not bear a chiral center). Inverting the structure, however, did result in even less probable Flack parameter. The calculated Flack parameter was hence deleted from the cif-file. The C-bound hydrogen atoms were included in calculated positions and treated as riding: C—H = 0.93–0.98 Å with Uiso(H) = 1.5 Ueq(C) for methyl groups and Uiso(H) = 1.2 Ueq(C) for all other C—H bonds. The hydrogen atom on N1 was located and refined without any restraints or constraints. The elongation of the ellipsoids of the tBu moiety suggests a rotational disorder of this group but modeling did not improve the refinement and was abandoned.

Comment

Structural reports of synthetic 4-fluorobenzohydrazide derivatives have started to appear in the literature only as recently as 2004; reports of such single crystal structure determinations continue to be released to date emphasizing their abiding relevance [5], [6], [7], [8], [9], [10], [11], [12], [13], [14], [15]. Hydrazide compounds and their role as ligands in complexes are studied due to widespread interest in their biological activities [16], for which the fluoro substituent is supposedly important for reasons of – inter alia – solubility, pharmaceutical application and in vivo monitoring. Hydrazides play further roles in the catalytic oxidation of alcohols [17], magnetic studies [18] and as chemsensors for pyrophosphate [19]. This contribuition is part of our interest in phenylhydrazide compounds and their characteristics including solid state properties.

The title compound crystallized in the monoclinic space group Cc with one molecule in the asymmetric unit. All bond lengths and angles of the hydrazide moiety do fall into the expected ranges as found in related molecules [1], [2], [3], [4], [5], [6], [7], [8], [9], [10], [11]. The N1—N2 distance is 1.386(4) Å (range in literature 1.369–1.395 Å), the N1—C(11) distance is 1.344(5) Å (range 1.329–1.359 Å), the C11 = O1 distance is 1.232(5) Å (range 1.216–1.245 Å) and the C16-F1 distance is 1.350(5) Å (range 1.345–1.365 Å); all apparently rather independent from further substitution on the phenyl rings adjacent to the hydrazide moiety (see top part of the figure). The angles between the two phenyl rings adjacent to the hydrazide moiety, on the other hand are rather distinct among this group of related compounds. This is apparently influenced by crystal packing effects and hydrogen bonding interactions. The angles range from almost coplanar (4.74°) to strongly out of plane (62.28°). In the title compound this value is 39.91°, i.e. on the larger side of the range. In the crystal lattice one medium strong hydrogen bonding interaction N1—H1N⋯O1 (D—A = 2.7886(6) Å) supported by a non-classical C12—H12⋯O1 (D—A = 3.3092(7) Å) hydrogen bonding interaction determines the crystal packing forming lines of molecules in a nearly zig-zag type arrangement of the molecule orientations along the crystallographic c axis (see bottom part of the figure; viewed along b). All molecules of the crystal are arranged in the same direction; i.e. the fluoro substituents of the molecules within the unit cell point roughly towards the origin of the coordinate system and the tBu substituents point away from it.

Acknowledgements

C.S. gratefully acknowledges support by the ERC project MocoModels.

References

Stoe & Cie: X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany, (2002).Suche in Google Scholar

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

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

Farrugia, L. J. : WinGX and ORTEP for Windows: an update. J. Appl. Cryst. 45 (2012) 849–854.10.1107/S0021889812029111Suche in Google Scholar

Zhang, Y.; Zhang, S.-P.; Wu, Y.-Y.; Shao, S.-C.: 4-Fluorobenzaldehyde salicylhydrazone. Acta Crystallogr. E62 (2006) o119–o120.10.1107/S1600536805040420Suche in Google Scholar

Dutkiewicz, G.; Narayana, B.; Samshuddin, S.;Yathirajan, H. S.; Kubicki, M.: Synthesis and crystal structures of two new Schiff base hydrazones derived from biphenyl-4-carbohydrazide. J.Chem.Cryst. 41(10) (2011) 1442–1446.10.1007/s10870-011-0118-3Suche in Google Scholar

Maheswari, R.; Manjula, J.; Gunasekaranc, B.; Bakiyaraj, G.:(E)-4-Methoxy-N′-(2,4,5-trifluorobenzylidene)-benzohydrazide monohydrate. IUCrData. 1 (2016) x160846.10.1107/S2414314616008464Suche in Google Scholar

Yathirajan, H. S.; Narayana, B.; Sunil, K.; Sarojini, B. K.;Bolte, M.: N′-[(1E)-(4-Fluorophenyl)methylene]-6-methoxy-2-naphthohydrazide. Acta Crystallogr. E63 (2007) o2565.10.1107/S160053680701820XSuche in Google Scholar

Narayana, B.; Sunil, K.; Yathirajan, H. S.; Sarojini, B. K.; Bolte, M.: 2-Bromo-N′-[(E)-(4-fluorophenyl)methylene]-5-methoxybenzohydrazide monohydrate. Acta Crystallogr. E63 (2007) o2948.10.1107/S1600536807024348Suche in Google Scholar

Wardell, S. M. S. V.; de Lima Ferreira, M.; de Souza, M. V. N.;Wardell, J. L.; Low, J. N.; Glidewell, C.: 2,4-Difluorobenzaldehyde benzoylhydrazone and 2,4-dichlorobenzaldehyde benzoylhydrazone are isostructural at 120 K with Z′ = 2: complex sheets built from N—H⋯O, C—H⋯O and C—H⋯π(arene) hydrogen bonds. Acta Crystallogr. C62 (2006) o118–o121.10.1107/S0108270106001995Suche in Google Scholar PubMed

Ali, H.; Khamis, N. A.; Yamin, B. M.: 1-(4-Fluoro-2-hydroxyphenyl)ethanone 4-nitrobenzoylhydrazone. Acta Crystallogr. E60 (2004) o1873–o1874.10.1107/S1600536804023657Suche in Google Scholar

He, D.-H.; Zhu, Y.-C.; Yang, Z.-R.: N′-(4-Fluorobenzylidene)-3,4,5-trimethoxybenzohydrazide. Acta Crystallogr. E64 (2008) o1648.10.1107/S1600536808023702Suche in Google Scholar PubMed PubMed Central

Wang, L.-H.; Tai, X.-S.: The crystal structure of (E)-N′-(quinolin-2-ylmethylene)furan-2-carbohydrazide monohydrate, C15H13N3O3. Z. Kristallogr. NCS 232 (2017) 1037–1038.Suche in Google Scholar

Maheswari, R., Manjula, J., Gunasekaran, B.: (E)-4-Chloro-N′-(2,4,5-trifluorobenzylidene)benzohydrazide. IUCrData 1 (2016) x160304.10.1107/S2414314616003047Suche in Google Scholar

Liu, M.; Duan, Y.; Wang, Y.; Zhang, W.-X.; Liu, S.: (E)-2-[2-(4-Fluorobenzylidene)-hydrazinocarbonyl]-N-isopropyl-benzamide. Acta Crystallogr. E65 (2009) o1599.10.1107/S1600536809022181Suche in Google Scholar PubMed PubMed Central

Rehman, S.-U.; Ikram, M.; Rehman, S.; Ullah, F.; Akhtar, G.: Synthesis, physicochemical, and biological studies of complexes of 2-aminobenzohydrazine with Co(II), Ni(II), Cu(II), and Zn(II) chlorides. Synth. React. Inorg. Met. Org. Chem. 40 (2010) 847–854.10.1080/15533174.2010.522648Suche in Google Scholar

Sutradhar, M.; Alegria, E. C. B. A.; Mahmudov, K. T.; Guedes da Silva, M. F. C.; Pombeiro, A. J. L.: Iron(III) and cobalt(III) complexes with both tautomeric (keto and enol) forms of aroylhydrazone ligands: catalysts for the microwave assisted oxidation of alcohols. RSC Adv. 6 (2016) 8079–8088.10.1039/C5RA25774CSuche in Google Scholar

Guo, M.; Wang, Y.; Wu, J.; Zhaoa, L.; Tang, J.: Structures and magnetic properties of dysprosium complexes: the effect of crystallization temperature. Dalton Trans. 46 (2017) 564–570.10.1039/C6DT04268FSuche in Google Scholar PubMed

Wang, J.; Liu, B.; Liu, X.; Panzner, M. J.; Wesdemiotisa, C.; Pang, Y.: A binuclear Zn(II)–Zn(II) complex from a 2-hydroxybenzohydrazide-derived Schiff base for selective detection of pyrophosphate. Dalton Trans. 43 (2014) 14142–14146.10.1039/C4DT01799DSuche in Google Scholar

Received: 2018-01-30
Accepted: 2018-04-12
Published Online: 2018-05-03
Published in Print: 2018-07-26

©2018 Muhammad Ikram et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of (E)-1-(4-(((E)-2-hydroxy-5-methylbenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C17H18N2O2
  3. Crystal structure of 1,3,5,7-tetraazaadamantane-1,3-diium 2,5-dicarboxyterephthalate, C16H18N4O8
  4. Crystal structure of guanidinium tetrabutyl-ammonium 5-hydroxyisophthalate dihydrate, C25H50N4O7
  5. Crystal structure of poly[aqua-(μ2-5-methoxyisophthalate-κ3O,O′:O′′)-(μ2-1,4-bis((1H-1,2,4-triazol-1-yl)methyl)benzene-κ2N:N′)nickel(II), NiC21H20N6O6
  6. Crystal structure of aqua-bis(3,4-dimethoxybenzoato-κ1O)-(2,2′-bipyridine-κ2N,N′)copper(II), C28H26CuN2O9
  7. Crystal structure of catena-poly[aqua-(μ2-(3,5-di(1H-imidazol-1-yl)-pyridine-κ2N:N′)-(μ2-2-(carboxylatomethyl)benzoato-κ2O:O′)] cadmium(II), C20H17CdN5O5
  8. The crystal structure of catena-poly[chlorido-(μ2-5-methyl-1,3,4-thiadiazole-2-thiolato-κ2S:N)mercury(II)], C3H3ClHgN2S2
  9. Crystal structure of (E)-2,4-dichloro-6-(((4-methyl-2-nitrophenyl)imino)methyl)phenol, C14H10Cl2N2O3
  10. Crystal structure of a new polymorph of bis[μ-1,3-bis(diphenylphosphino)propane-κ2P:P′-disilver(I)] bis(tetrafluoroborate), [Ag(dppp)]2(BF4)2, C54H52Ag2B2F8P4
  11. The crystal structure of 2-phenyl-4,6-bis(R-tert-butylsulfonamido)-1,3,5-triazine – ethyl acetate (2/1), C38H58N10O6S4
  12. Crystal structure of 6-amino-8-(2-methoxy-phenyl)-2-methyl-2,3,8,8a-tetrahydro-1H-iso-quinoline-5,7,7-tricarbonitrile monohydrate, C20H21N5O2
  13. Crystal structure of methyl (1-phenylethyl)carbamate, C10H13NO2
  14. Crystal structure of dimethanol-(μ2-squarato-κ2O:O′)-tetrakis(tri-p-tolylphosphane-κP)disilver(I) – methanol (1/2), C92H98Ag2O8P4
  15. Crystal structure of catena-poly[bis(μ2-1,4-bis(triazol-1-ylmethyl)benzene-κ2N:N′)-bis(5-tert-butyl-isophthalate-κO)copper(II)]tetrahydrate, C36H46CuN6O12
  16. Crystal structure of 4-aminopyridinium 4-acetyl-(pyridin-4-yl)-1H-1,2,3-triazol-5-olate monohydrate, C14H16N6O3
  17. Crystal structure of 2-(8-bromo-2-phenylimidazo[1,2-α]pyridin-3-yl)-6,7-dimethyl-3-phenylquinoxaline, C29H21BrN4
  18. Crystal structure of aqua(1-(2-pyridyl)ethanone oxime-κ2N,N′)(1-(2-pyridyl)ethanone oximato-κ2N,N′) nitrate monohydrate, C14H19N5O7Cu
  19. Crystal structure of poly[tetraaqua-(μ4-oxalato-κ4O,O′:O′′,O′′′)-(μ8-benzene-1,2,4,5-tetracarboxylato-κ8O1:O2:O3:O4:O5:O6:O7:O8)yttrium(III)], C6H5O8Y
  20. Crystal structure of bis{catena-poly[(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′)silver(I)]} diaqua-bis(5-(4-carboxyphenyl)pyridine-2-carboxylato-κ2N,O)-(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′)disilver(I) octahydrate, C31H35Ag2N4O9
  21. Crystal structure of (E)-N-(2-(benzylamino)-2-oxo-1-(4-oxo-4H-chromen-3-yl)ethyl)-N-(4-bromophenyl)-3-chloroacrylamide hydrate, C27H22BrClN2O5
  22. Crystal structure of catena-poly[octaaqua-bis(μ2-4,6-dicarboxyisophthalate-κ2O:O′)cadmium(II)disodium(I)] dihydrate, C20H28CdNa2O26
  23. Crystal structure of acetonitrile{bis(2-benzimidazolylmethyl)amine-κ3N,N′,N′′}-{maleato-κO}zinc(II) perchlorate - acetonitrile (1/1), C24H24ClN7O8Zn
  24. Crystal structure of 2-amino-4-(3,5-dibromo-4-hydroxyphenyl)-7-methyl-5-oxo-2H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C16H10Br2N2O4
  25. Crystal structure of catena-poly[diaqua-(μ2-3,5-bis(pyridin-4-ylmethoxy)benzoate-κ2N:O) manganese(II)] tetrahydrate [(3,5-bis-(pyridin-4-ylmethoxy)-benzoic-κ1Oκ1N) manganese(II)] trihydrate, C38H42MnN4O14
  26. The crystal structure of 2-carboxybenzaldehyde-2-phenylacetohydrazone, C16H14N2O3
  27. The crystal structure of poly[μ2-aqua-(μ2-2-naphthylamine-1-sulfonato-κ3O,O′:O′′)sodium(I)], C10H10N1O4S1Na
  28. The crystal structure of phthalazin-1(2H)-one, C8H6N2O1
  29. Crystal structure of 3,5-bis(trifluoromethyl)benzyl(Z)-N-(adamantan-1-yl)morpholine-4-carbothioimidate, C24H28F6N2OS
  30. Crystal structure of diazido-bis(μ2-pyridin-2-ylmethanolato-κ2N:O)-bis(pyridin-2-ylmethanolato-κ2N,O)dicobalt(III) – methanol (1/3), C27H35Co2N10O7
  31. Crystal structure of N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(2,2,2-trifluoroethoxy)-2-pyridinesulfonamide, C14H14F3N5O6S
  32. Crystal structure of 1-phenyl-N′-(1-phenyl-5-(thiophen-2-yl)-1H-pyrazole-3-carbonyl)-5-(thiophen-2-yl)-1H-pyrazole-3-carbohydrazide, C28H20N6O2S2
  33. The crystal structure of poly[bis(4-hydroxybenzoato-κO)-(μ2-4,4′-bipyridine-κ2N:N′)copper(II)] hydrate, C24H20N2O7Cu
  34. Crystal structure of poly[μ3-5-(4-(2,6-di(pyridine-2-yl)pyridine-4-yl)phenoxy)isophthalato-κ5O:O′,O′′:N,N′,N′′cobalt(II)], C29H17CoN3O5
  35. Crystal structure of poly[μ3-5-(4-(2,6-di(pyridine-2-yl)pyridine-4-yl)phenoxy)isophthalato-κ6O:O′,O′′:N,N′,N′′)cobalt(II)] C29H17CoN3O5
  36. Crystal structure of diaqua-(acetato-κ3O,O′:O′′)-(μ3-4,6-di(1H-imidazol-1-yl)isophthalato-κ4O:O′:O′′,O′′′)lanthanum(III), C16H15LaN4O8
  37. Synthesis and crystal structure of 6-carboxy-1-(3,5-dicarboxyphenyl)-1H-benzo[d]imidazol-3-ium-5-carboxylate dihydrate, C18H12N2O8
  38. Crystal structure of (E)-2-hydroxybenzaldehyde O-(2-(((E)-(4-(dimethylamino)benzylidene)amino)oxy)ethyl)oxime, C18H21N3O3
  39. Crystal structure of bis{2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}zinc(II), C32H30N4O4Zn
  40. Crystal structure of bis(9-aminoacridin-10-ium) tetrachloridocuprate(II) monohydrate, C26H24Cl4CuN4O
  41. The crystal structure of 4-tert-butyl-N′-[(E)-(4-fluoro-3-methoxyphenyl)methylidene]benzohydrazide, C19H21F1N2O2
  42. Crystal structure of (E)-3-(3-(5-methyl-1-4-tolyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-one, C31H26N8O
  43. Crystal structure of (E)-N′-(4-methoxybenzylidene)-5-methyl-1-(4-tolyl)-1H-1,2,3-triazole-4-carbohydrazide, C19H19N5O2
  44. Crystal structure and molecular packing of O-ethyl (2-chlorophenyl)carbamothioate, C9H10ClNOS
  45. Crystal structure of pyrene-2-carbaldehyde, C17H10O
  46. Crystal structure of (E)-2,4-diiodo-6-(4-methyl-2-nitrostyryl)phenol, C14H10I2N2O3
  47. Crystal structure of (E)-2,4-dichloro-6-(((4-methoxy-2-nitrophenyl)imino)methyl)phenol, C14H10Cl2N2O4
  48. Crystal structure of (E)-2-bromo-4-chloro-6-(4-methoxy-2-nitrostyryl)phenol, C14H10BrClN2O4
  49. Crystal structure of (E)-4,6-diiodo-2-(((4-methoxy-2-nitrophenyl)imino)methyl)-3-methylphenol, C14H10I2N2O4
  50. The crystal structure of 7-bromo-1-cyclopropyl-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid an intermediate of the ozenoxacin synthesis, C14H12BrNO3
  51. Crystal structure of bis(N-(1-(pyrazin-2-yl)ethylidene)nicotinohydrazonato-κ3N,N′,O)copper(II) C24H20N10O2Cu
  52. Crystal structure of diaqua-dinitrato-k2O,O′((Z)-N-((E)-1-(pyrazin-2-yl)ethylidene)nicotinohydrazonato-k3N,N′,O)europium(II), C12H14N7O9Eu
  53. Crystal structure of ethyl 4-amino-5-(5-methyl-1-(4-tolyl)-1H-1,2,3-triazole-4-carbonyl)-2-(phenylamino)thiophene-3-carboxylate, C24H23N5O3S
  54. The crystal structure of acridin-10-ium2-carboxybenzoate, C21H15NO4
  55. The crystal structure of 3-((phenylamino)methylene)-1,5-dioxaspiro[5.5]undecane-2,4-dione, C16H17N1O4
  56. Crystal structure of 12-chloro-5,6,7,12-tetrahydrodibenzo[c,f][1,5]oxastibocine, C14H12ClOSb
  57. Crystal structure of 4-((1,3-dioxoisoindolin-2-yl)methyl)phenethyl 4-methylbenzenesulfonate, C24H21NO5S
  58. Crystal structure of 3-methyl-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C9H8N2OS
  59. Crystal structure of tert-butyl (2-(4-oxo-2-thioxo-1,4-dihydroquinazolin-3(2H)-yl)ethyl)carbamate, C15H19N3O3S
  60. Crystal structure of ethyl 5-formyl-3,4-dimethylpyrrole-2-carboxylate–1-(propan-2-ylidene)thiosemicarbazide (1/1), C14H22N4O3S
  61. Crystal structure of bis-(N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-3-hydroxybenzohydrazide-κ2O,N)copper(II) – dimethylformamide (1/2), C40H50N8O10Cu
  62. Crystal structure of bis(acetato-κO)bis{2-((1H-tetrazol-1-yl)methyl)-1H-benzo[d]imidazole-κN}zinc(II), C22H22N12O4Zn
  63. Crystal structure of 4-phenyl-3-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)-1H-1,2,4-triazole-5(4H)-thione, C17H14N6S
  64. Crystal structure of (Z)-N-(4-nitrophenyl)-3-phenyl-3-(phenylamino)acrylamide, C21H17N3O3
  65. Crystal structure of 1,1′-(pentane-1,5-diyl)bis(3-methyl-1H-imidazol-3-ium)bis(hexafluorophosphate), C13H22F12N4P2
  66. Synthesis and crystal structure of bis(furan-2-ylmethanaminium)-catena-[bis(μ2-phthalato-κ2O:O′)cobalt(II)], C26H24CoN2O10
  67. Crystal structure of methyl (R)-4-(o-chlorobenzoyl)-1-thia-4-azaspiro[4.5]decane-3-carboxylate, C17H20ClNO3S
  68. Crystal structure of 2-[[4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]ethyl]phenyl] methyl]-1H-isoindole-1,3(2H)-dione, C28H29N3O3
  69. The crystal structure of benzenaminium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate hydrate, C21H19NO8S
  70. Crystal structure of semiconducting potassium poly[(μ2-tetraselenido-κ2Se1:Se4)(μ2-pentaselenido-κ1Se1:Se1)argentate(I)], K3AgSe9
  71. Crystal structure of 2-isopropyl-8-methyl-phenanthrene-3,4-dione, C18H16O2
  72. Crystal structure of 2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione, C19H22O2
  73. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-4-bromophenol, C14H13BrN2O
  74. Crystal structure of 1,1-di(4-cyanophenyl)-2,2-diphenylethene, C28H18N2
  75. Crystal structure of bis(hydroxylamido-κ2O,N)-oxido(1H-pyrazole-3-carboxylato-κ2O,N)vanadium(V), C4H7N4O5V
  76. The crystal structure of In1.2B3O5.6(OH)1.4
  77. The crystal structure of chlorido(2-(1H-pyrazol-3-yl)phenolato-κ2N,O)(2-(1H-pyrazol-3-yl)phenol-κN)copper(II), C18H15ClCuN4O2
  78. Crystal structure of 1-heptylpyridazin-1-ium iodide, C11H19N2I
  79. The crystal structure of N-butylpyridinium bis(μ2-dichlorido)-tetrachloridodicopper(II), C18H28N2Cu2Cl6
  80. Crystal structure of 6-hydroxy-5-((2-hydroxy-6-oxocyclohex-1-en-1-yl)(4-methoxyphenyl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, C20H22N2O6
  81. Crystal structure of bis(acetonitrile)-diaqua-dichloridoiron(II), C4H10Cl2N2O2Fe
Heruntergeladen am 30.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2017-0408/html
Button zum nach oben scrollen