Home Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
Article Open Access

Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn

  • See Mun Lee , Kong Mun Lo and Edward R.T. Tiekink ORCID logo EMAIL logo
Published/Copyright: September 9, 2019
Download Article (PDF)
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 6

Abstract

C24H20Br4N2Sn, monoclinic, P21/n (no. 14), a = 9.3186(1) Å, b = 16.2615(1) Å, c = 16.8482(1) Å, β = 100.748(1)°, V = 2508.29(4) Å3, Z = 4, Rgt(F) = 0.0254, wRref(F2) = 0.0688, T = 100(2) K.

CCDC no.: 1948395

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:Colourless prism
Size:0.22 × 0.12 × 0.07 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:15.7 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:67.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:30929, 4485, 0.044
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4381
N(param)refined:280
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Sn0.90693(2)0.80694(2)0.46094(2)0.01015(8)
Br10.80742(3)0.85195(2)0.59351(2)0.02153(10)
Br21.18629(3)0.86061(2)0.49199(2)0.01685(9)
Br30.61849(3)0.38481(2)0.40064(2)0.02523(10)
Br40.19446(3)0.94430(2)0.24467(2)0.02203(10)
N10.9227(3)0.74801(15)0.33496(13)0.0146(5)
N20.6826(2)0.74562(16)0.40155(14)0.0140(5)
C10.9890(3)0.69134(17)0.51694(17)0.0149(6)
H1A1.08810.68210.50540.018*
H1B0.99880.69730.57620.018*
C20.8997(3)0.61702(18)0.49149(17)0.0150(6)
C30.9281(3)0.56959(19)0.42624(17)0.0159(6)
H31.00610.58460.40010.019*
C40.8437(3)0.50124(19)0.39961(17)0.0180(6)
H40.86280.46980.35520.022*
C50.7319(3)0.47960(19)0.43854(17)0.0168(6)
C60.7023(3)0.5238(2)0.50419(18)0.0183(6)
H60.62660.50700.53140.022*
C70.7855(3)0.59280(19)0.52899(17)0.0165(6)
H70.76410.62450.57270.020*
C80.8480(3)0.92369(18)0.40082(17)0.0150(6)
H8A0.87280.96870.44060.018*
H8B0.90720.93150.35840.018*
C90.6906(3)0.93006(18)0.36335(16)0.0145(6)
C100.6383(3)0.8981(2)0.28615(16)0.0184(6)
H100.70530.87410.25680.022*
C110.4920(3)0.9006(2)0.25182(17)0.0189(6)
H110.45800.87740.20000.023*
C120.3950(3)0.93752(18)0.29436(17)0.0157(6)
C130.4414(3)0.96956(19)0.37062(17)0.0154(6)
H130.37380.99400.39930.019*
C140.5893(3)0.96530(18)0.40475(16)0.0157(6)
H140.62210.98690.45740.019*
C151.0446(3)0.7537(2)0.30375(17)0.0176(6)
H151.12520.78360.33280.021*
C161.0580(4)0.7177(2)0.23069(18)0.0218(7)
H161.14530.72310.20970.026*
C170.9406(4)0.6738(2)0.18967(18)0.0256(7)
H170.94680.64790.13990.031*
C180.8142(4)0.6674(2)0.22070(18)0.0221(7)
H180.73240.63810.19220.026*
C190.8080(3)0.70469(19)0.29462(17)0.0165(6)
C200.6776(3)0.70164(18)0.33275(17)0.0156(6)
C210.5517(3)0.6578(2)0.2992(2)0.0237(7)
H210.54940.62590.25180.028*
C220.4306(4)0.6614(2)0.3357(2)0.0282(8)
H220.34470.63160.31380.034*
C230.4354(3)0.7086(2)0.4040(2)0.0251(7)
H230.35230.71300.42890.030*
C240.5634(3)0.74942(19)0.43552(17)0.0174(6)
H240.56720.78140.48310.021*

Source of material

The melting point of the compound was measured on a Melt-Temp II digital melting point apparatus and was uncorrected. The IR spectrum was measured on a Bruker Vertex 70v FTIR spectrophotometer from 4000 to 400 cm−1. The 1H and 13C{1H} NMR spectra were recorded in CDCl3 solution on a Bruker Ascend 400 MHz NMR spectrometer with chemical shifts relative to tetramethylsilane.

Di(4-bromobenzyl)tin dibromide was synthesized by the direct reaction of 4-bromobenzyl bromide (Merck) and metallic tin powder (Merck) in toluene according to a literature procedure [5]. Di(4-bromobenzyl)tin dibromide (0.62 g, 1.0 mmol) and 2,2′-bipyridine (Aldrich, 0.16 g, 1.0 mmol) were heated in 95% ethanol (30 mL) and stirred for 2 h. After filtration, the filtrate was evaporated slowly until colourless crystals were formed. Yield: 0.42 g (54.2%). M.pt: 465–467 K. IR (cm−1) 1586 (m) ν(CN), 1482, 1097 (s) ν(CN), 467 (m) ν(SnN). 1H NMR (DMSO-d6, ppm): δ 3.10 (s, 2H, Ph—CH2), 7.18–7.32 (m, 2H, Ph—H), 7.49–7.60 (m, 2H, Ph—H), 7.77–7.87 (m, 1H, bipy-H), 8.09–8.13 (m, 1H, bipy-H), 8.45–8.48 (d, 1H, bipy-H), 8.76–8.80 (m, 1H, bipy-H). 13C{1H} NMR (DMSO-d6, ppm): δ 71.1 (CH2), 118.1, 125.5, 130.8, 132.1 (Ph—C), 121.8, 126.0. 139.3, 149.0, 153.7 (bipy-C).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The maximum and minimum residual electron density peaks of 0.90 and 1.11 eÅ−3, respectively, were located 1.07 and 0.98 Å from the Sn atom, respectively.

Comment

Very recently, the crystal and molecular structures of the organotin precursor, (4-BrC6H4CH2)2SnBr2, featured in the title compound, (4-BrC6H4)2SnBr2(2,2′-bipyridyl), was described [6]. By contrast to the approximately 50 analogous structures of bipyridyl-type (NN) ligands with R2SnCl2, there are only three species of the general formula R2SnBr2(NN) reported, namely R = Me, NN = 4,4′-bis(but-3-en-1-yl)-2,2′-bipyridine [7], R = CF2CF3, NN = 1,10-phenanthroline [8] and R = 3-BrC6H4CH2, NN = 4,7-diphenyl-1,10-phenanthroline [9]. Given this paucity of data for R2SnBr2(NN), the title compound was synthesised and characterised crystallographically.

The molecule is illustrated in the figure (70% displacement ellipsoids) and features a distorted octahedral geometry for the tin atom based on two carbon atoms of the substituted benzyl groups, two bromide atoms and two nitrogen atoms of the 2,2′-bipyridyl molecule. In the Br2C2N2 donor set, the benzyl-carbon atoms are mutually trans, and each of the bromide atoms is trans to a pyridyl-nitrogen atom. While there is a definite disparity in the Sn—Br bond lengths [Sn—Br1 = 2.6752(3) Å and Sn—Br2 = 2.7027(3) Å], the Sn—N bond lengths [Sn—N1 = 2.358(2) Å and Sn—N2 = 2.363(2) Å] are equal within experimental error. Non-systematic variations in geometric parameters in related organotin compounds of bipyridyl-type ligands were shown by DFT calculations to be the result of molecular packing considerations rather than having any chemical significance [10], [11]. The major distortions from the ideal octahedral geometry in the cis angles is seen in the N1—Sn—N2 chelate angle of 69.27(8)°, and in terms of trans angles, in the N1—Sn—Br1 angle of 162.19(6)°. Globally, the phenyl rings of the benzyl substituents are folded over the molecule to be orientated towards the 2,2′-bipyridyl molecule. This is reflected in close inter-centroid ring separations of 3.5663(17) Å between the chelate and C2-phenyl rings, and 3.6720(17) Å between the N2-pyridyl and C9-phenyl rings. The importance of stabilising interactions between chelate and organic rings is now well documented [12], [13], at least in the context of intermolecular interactions.

As mentioned above, the strucure of (4-BrC6H4CH2)2SnBr2 became available recently [6]. The molecule has crystallographic two-fold symmetry with the tetrahedrally coordinated tin atom lying on the axis. The Sn—Br bond distances are each 2.5143(2) Å, that is, considerably shorter than those in the title compound, reflecting the influence of the increased coordination number at the tin atom in the title structure. Such a trend was not as pronounced in the recently described structure of the sulphoxide adduct, (4-BrC6H4CH2)2SnBr2(O=S(CH2Ph)2 [14], where only one of the Sn—Br bond lengths elongated significantly, i.e. the axially-bound bromide atom in a trigonal-bipyramidal geometry.

The three-dimensional molecular packing is sustained by weak non-covalent interactions. Thus, supramolecular layers parallel to (1 0 −1) are constructed by π⋯π interactions between centrosymmetrically-related C2-phenyl rings [Cg(C2—C7)⋯Cg(C2—C7)i = 3.7569(17)° for symmetry operation (i) 2 − x, 1 − y, 1 − z] and end-on C—Br⋯π(N2-pyridyl) interactions [C5—Br3⋯Cg(N2,C20—C24)ii: Br3⋯Cg(N2,C20—C24)ii = 3.9096(13) Å, C5⋯Cg(N2,C20—C24)ii = 5.563(3) Å with angle at Br3 = 143.56(9)° for (ii) 3/2 − x, −1/2 + y, 1/2 − z]. The connections between layers are of the type C—H⋯Br [C16—H16⋯Br1iii: = H16⋯Br1iii = 2.95 Å, C16⋯Br1iii = 3.746(4) Å with angle at H16 = 142° for (iii) 1/2 + x, 3/2 − y, −1/2 + z] and phenyl-Br⋯Br(phenyl) [Br3⋯Br4iv = 3.5737(4) Å for (iv) 1/2 − x, −1/2 + y, 1/2 − z]. The importance of halogen bonding in crystals has been reviewed recently [15].

To evaluate the molecular packing further and to compare this to the structure of the all-chloro analogue (4-ClC6H4)2SnCl2(2,2′-bipyridyl) [16], Crystal Explorer 17 [17] was employed following established protocols [18] to calculate the Hirshfeld surfaces as well as the two-dimensional fingerprint plots (full and delineated into individual contacts). Nearly equal contributions to the calculated Hirshfeld surface are provided by H⋯H [40.2%] and H⋯Br/Br⋯H [40.8%] contacts. The next most significant contributions are due to H⋯C/C⋯H [11.1%] and then fall away to Br⋯C/C⋯Br [3.1%], Br⋯Br [2.3%] and C⋯C [1.9%]. When compared to the all-chloro derivative [16], the H⋯H [42.3%] and H⋯Cl/Cl⋯H [38.7%] contacts, respectively, increase and decrease by approximately the same extent. The contribution of contacts between halogen(Cl) and C atoms is reduced [2.0%], but the percentage contribution of the other identified contacts remain about the same.

Funding source: Sunway University Sdn Bhd

Award Identifier / Grant number: STR-RCTR-RCCM-001-2019

Funding statement: Sunway University Sdn Bhd is thanked for financial support of this work through Grant no. STR-RCTR-RCCM-001-2019.

References

1. Rigaku Oxford Diffraction: CrysAlis PRO. Rigaku Corporation, Oxford, UK (2018).Search in Google Scholar

2. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

4. Farrugia, L. J.: WinGX and ORTEP for Windows: an update. J. Appl. Crystallogr. 45 (2012) 849–854.10.1107/S0021889812029111Search in Google Scholar

5. Sisido, K.; Takeda, Y.; Kinugawa, Z.: Direct synthesis of organotin compounds I. di- and tribenzyltin chlorides. J. Am. Chem. Soc. 83 (1961) 538–541.10.1021/ja01464a008Search in Google Scholar

6. Lee, S. M.; Lo, K. M.; Tiekink, E. R. T.: Crystal structure of dibromidobis(4-bromobenzyl)tin(IV), C14H12Br4Sn. Z. Kristallogr. NCS 234 (2019) 947–948.10.1515/ncrs-2019-0162Search in Google Scholar

7. Haberecht, M. C.; Bats, J. W.: Private communication to the Cambridge Structural Database. Refode: SODYER (2014).Search in Google Scholar

8. Klösener, J.; Wiesemann, M.; Niemann, M.; Neumann, B.; Stammler, H.-G.; Hoge, B.: Synthesis of mono-, bis- and tris(pentafluoroethyl)tin derivatives, (C2F5)4-nSnXn (X=Ph, Me, Cl, Br, Cp; n = 1-3). Chem. Eur. J. 23 (2017) 8295–8303.10.1002/chem.201701270Search in Google Scholar PubMed

9. Bhaskar, C.; Chandrasekar, S.; Mohandas, T.; Butcher, R. J.: Di-bromido-bis-(3-bromo-benzyl-κC)(4,7-diphenyl-1,10-phenanthroline-κ2N,N′)tin(IV). IUCrData 4 (2019) x190336.10.1107/S2414314619003365Search in Google Scholar

10. Buntine, M. A.; Hall, V. J.; Kosovel, F. J.; Tiekink, E. R. T.: Influence of crystal packing on molecular geometry: a crystallographic and theoretical investigation of selected diorganotin systems. J. Phys. Chem. A 102 (1998) 2472–2482.10.1021/jp9728722Search in Google Scholar

11. Buntine, M. A.; Hall, V. J.; Tiekink, E. R. T.: The crystal and molecular structures of R2SnCl2(1,10-phenanthroline), R = iPr, Cy, CH2Ph and R2 = Me, Ph: a comparison between solid state and theoretical structures. Z. Kristallogr. 213 (1998) 669–678.10.1524/zkri.1998.213.12.669Search in Google Scholar

12. Malenov, D. P.; Janjić, G. V.; Medaković, V. B.; Hall, M. B.; Zarić, S. D.: Noncovalent bonding: stacking interactions of chelate rings of transition metal complexes. Coord. Chem. Rev. 345 (2017) 318–341.10.1016/j.ccr.2016.12.020Search in Google Scholar

13. Tiekink, E. R. T.: Supramolecular assembly based on “emerging” intermolecular interactions of particular interest to coordination chemists. Coord. Chem. Rev. 345 (2017) 209–228.10.1016/j.ccr.2017.01.009Search in Google Scholar

14. Lee, S. M.; Lo, K. M.; Tiekink, E. R. T.: Crystal structure of (dibenzyl sulphoxide-κO)dibromido-bis(4-bromobenzyl-κC)tin(IV), C28H26Br4OSSn. Z. Kristallogr. NCS 234 (2019). doi: 10.1515/ncrs-2019-0541.10.1515/ncrs-2019-0541Search in Google Scholar

15. Cavallo, G.; Metrangolo, P.; Milani, R.; Pilati, T.; Priimagi, A.; Resnati, G.; Terraneo, G.: The halogen bond. Chem. Rev. 116 (2016) 2478–2601.10.1021/acs.chemrev.5b00484Search in Google Scholar PubMed PubMed Central

16. Lee, S. M.; Lo, K. M.; Tiekink, E. R. T.: Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn. Z. Kristallogr. NCS 234 (2019). doi: 10.1515/ncrs-2019-0508.10.1515/ncrs-2019-0508Search in Google Scholar

17. Turner, M. J.; McKinnon, J. J.; Wolff, S. K.; Grimwood, D. J.; Spackman, P. R.; Jayatilaka, D.; Spackman, M. A.: Crystal Explorer v17. The University of Western Australia, Australia (2017).Search in Google Scholar

18. Tan, S. L.; Jotani, M. M.; Tiekink, E. R. T.: Utilizing Hirshfeld surface calculations, non-covalent interaction (NCI) plots and the calculation of interaction energies in the analysis of molecular packing. Acta Crystallogr. E75 (2019) 308–318.10.1107/S2056989019001129Search in Google Scholar PubMed PubMed Central

Received: 2019-07-18
Accepted: 2019-08-21
Published Online: 2019-09-09
Published in Print: 2019-11-26

©2019 See Mun Lee et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′] zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
  5. Crystal structure of 4,4′-(hydrazonomethylene)diphenol dihydrate, C13H16N2O4
  6. Crystal structure of 4-methoxyphenyl-3-phenylpropiolate, C16H12O3
  7. Crystal Structure of tris(tetrakis{1-vinyl-1H-imidazole-κN}copper(II)) bis[tri-μ2-bromido-tetrabromido-bis(1-vinyl-1H-imidazole-κN)tetracopper(I)], C80H96N32Cu11Br14
  8. Crystal structure of (E)-2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)-N′-(quinoxalin-2-ylmethylene)benzohydrazide, C37H36N6O2
  9. Crystal structure of 4-(1-phenylimidazo[1,5-a]pyridin-3-yl)benzoic acid (C20H14N2O2)
  10. Crystal structure of 3-fluoro-3-methyl-1-((2-nitrophenyl)sulfonyl)-5,5-diphenylpiperidine, C24H23FN2O4S
  11. Crystal structure of dimethyl 3,12-dibenzyl-6,10-diphenyl-3,12-diazapentacyclo [6.3.1.02.7.04.11.05.9]-dodecane-7,11-dicarboxylate — acetone (2/1), C40H38N2O2 ⋅ 0.5C3H6O
  12. Crystal structure of poly[(μ2-2-(1H-1,2,4-triazol-1-yl)benzoato-κ4O:O′:N:N′)silver(I)] monohydrate, C9H8AgO3N3
  13. Crystal structure of poly[(μ2-9H-carbazole-3,6-dicarboxylate-κ4O1,O2:O3,O4)(μ2-1,3-di(pyridin-4-yl)propane-κ2N:N′)cadmium(II)]monohydrate, C27H23N3O5Cd
  14. The synthesis and crystal structure of bis(2-(benzo[d]thiazol-2-yl)-5-methylbenzen-1-ido-κ2C,N)-(N,N′-diethyldithiocarbamato-κ2S,S′)iridium(III), C33H30N3S4Ir
  15. The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
  16. Synthesis and crystal structure of poly[(μ2-nitrato-κ4O,O′:O′,O′′)-nitrato-κO-(μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)cadmium(II)], C14H14N6O6Cd
  17. Crystal structure of ethyl (Z)-(4-oxo-4-phenylbut-2-en-2-yl)glycinate, C14H17NO3
  18. Halogen bonds in the crystal structure of 5-bromo-3,4′-bipyridine – 1,4-diiodotetrafluorobenzene (2/1), C26H14Br2F4I2N4
  19. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-tetrakis(μ2-3-(phenylsulfonamido)propanoato-κ2O:O′)-bis(3-(phenylsulfonamido)propanoato-κ2O,O′)digadolinium(III) – 2,2′-bipyridine (1/1), C84H84Gd2N12O24S6
  20. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ2O:O′)bis(μ2-pyrazin-κ2N:N′)silver(I)], C14H16Ag2N5O8S2
  21. The crystal structure of 1,6-di-tert-butyl-1,1,3,3,4,4,6,6-octamethyl-2,2,5,5-tetrakis (trimethylsilyl)hexasilane, C28H78Si10
  22. Crystal structure of discandium triruthenium tetrasilicide, Sc2Ru3Si4
  23. Crystal structure of poly[(μ2-4-amino-1,5-naphthalenedisulfonato-κ4O,N:O′, N′)bis(μ2-hexamethylenetetramino-κ2N;N′)silver(I)], {C22H30Ag2N9O6S2}n
  24. Crystal structure of diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-κ4O,O′,N,N′)]zinc(II) dihydrate, C13H18N4O12Zn
  25. The crystal structure of poly [(μ3-N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide-κ3-O:N:N′)-(p-toluenesulfonato-κ2O,O′)silver(I)], C25H27Ag1N4O5S
  26. The crystal structure of 1,2-bis(3-bromophenoxy) ethane, C14H12Br2O2
  27. The crystal structure of 4-(pyren-1-yl)butyl-3-nitrobenzoate, C27H21NO4
  28. Crystal structure of bis[(2-(4-chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ1O) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Cl2N4NiO8
  29. The crystal structure of 1,5-dinitro-2,3,4-trichlorobenzene, C6H1Cl3N2O4
  30. The crystal structure of the solid solution of 3,5-dinitropyrazole and 4-chlorine-3,5-dinitropyrazole, C3H1.24Cl0.76N4O4
  31. The cocrystal structure of 4-nitropyrazole — acetic acid (1/1), C5H7N3O4
  32. The crystal structure of propan-2-one O-(2,4,6-trinitrophenyl) oxime, C9H8N4O7
  33. The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
  34. Crystal structure of (acetic acid-κ1O)-bis(μ2-2-chlorobenzoato-κ2O:O′)-(2-chlorobenzoato-κ1O)-(μ2-hydroxy-κ2O:O)-bis(1,10-phenanthroline-κ2N,N′)dimanganese(II) — methanol (1/1), C48H37Cl3Mn2N4O10
  35. Crystal structure of 3-methyl-2-phenyl-1,8-naphthyridine, C15H12N2
  36. Crystal structure of chlorido-(5-acetyl-2-(5-methylpyridin-2-yl)benzen-1-ido-κ2C,N)-pyridine-κN-palladium(II), C19H17ClN2OPd
  37. Crystal structure of (4-methyl-benzoato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C24H45ClN4NiO7
  38. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) 1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl(potassium, rubidium) — ammonia (1/2), [K0.3Rb0.7(18-crown-6)]Cp*⋅2 NH3, C22H45K0.3N2O6Rb0.7
  39. Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
  40. Crystal structure of (E)-N′-((1,6-dihydropyren-1-yl)methylene)isonicotinohydrazide — methanol (1/1), C24H19N3O2
  41. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ3N,O:O′)-(μ4-hexamethylenetetramino-κ4N:N′:N′′:N′′′)disilver(I)] monohydrate, C12H21Ag2N5O8S2
  42. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
https://doi.org/10.1515/ncrs-2019-0507
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′] zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
  5. Crystal structure of 4,4′-(hydrazonomethylene)diphenol dihydrate, C13H16N2O4
  6. Crystal structure of 4-methoxyphenyl-3-phenylpropiolate, C16H12O3
  7. Crystal Structure of tris(tetrakis{1-vinyl-1H-imidazole-κN}copper(II)) bis[tri-μ2-bromido-tetrabromido-bis(1-vinyl-1H-imidazole-κN)tetracopper(I)], C80H96N32Cu11Br14
  8. Crystal structure of (E)-2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)-N′-(quinoxalin-2-ylmethylene)benzohydrazide, C37H36N6O2
  9. Crystal structure of 4-(1-phenylimidazo[1,5-a]pyridin-3-yl)benzoic acid (C20H14N2O2)
  10. Crystal structure of 3-fluoro-3-methyl-1-((2-nitrophenyl)sulfonyl)-5,5-diphenylpiperidine, C24H23FN2O4S
  11. Crystal structure of dimethyl 3,12-dibenzyl-6,10-diphenyl-3,12-diazapentacyclo [6.3.1.02.7.04.11.05.9]-dodecane-7,11-dicarboxylate — acetone (2/1), C40H38N2O2 ⋅ 0.5C3H6O
  12. Crystal structure of poly[(μ2-2-(1H-1,2,4-triazol-1-yl)benzoato-κ4O:O′:N:N′)silver(I)] monohydrate, C9H8AgO3N3
  13. Crystal structure of poly[(μ2-9H-carbazole-3,6-dicarboxylate-κ4O1,O2:O3,O4)(μ2-1,3-di(pyridin-4-yl)propane-κ2N:N′)cadmium(II)]monohydrate, C27H23N3O5Cd
  14. The synthesis and crystal structure of bis(2-(benzo[d]thiazol-2-yl)-5-methylbenzen-1-ido-κ2C,N)-(N,N′-diethyldithiocarbamato-κ2S,S′)iridium(III), C33H30N3S4Ir
  15. The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
  16. Synthesis and crystal structure of poly[(μ2-nitrato-κ4O,O′:O′,O′′)-nitrato-κO-(μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)cadmium(II)], C14H14N6O6Cd
  17. Crystal structure of ethyl (Z)-(4-oxo-4-phenylbut-2-en-2-yl)glycinate, C14H17NO3
  18. Halogen bonds in the crystal structure of 5-bromo-3,4′-bipyridine – 1,4-diiodotetrafluorobenzene (2/1), C26H14Br2F4I2N4
  19. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-tetrakis(μ2-3-(phenylsulfonamido)propanoato-κ2O:O′)-bis(3-(phenylsulfonamido)propanoato-κ2O,O′)digadolinium(III) – 2,2′-bipyridine (1/1), C84H84Gd2N12O24S6
  20. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ2O:O′)bis(μ2-pyrazin-κ2N:N′)silver(I)], C14H16Ag2N5O8S2
  21. The crystal structure of 1,6-di-tert-butyl-1,1,3,3,4,4,6,6-octamethyl-2,2,5,5-tetrakis (trimethylsilyl)hexasilane, C28H78Si10
  22. Crystal structure of discandium triruthenium tetrasilicide, Sc2Ru3Si4
  23. Crystal structure of poly[(μ2-4-amino-1,5-naphthalenedisulfonato-κ4O,N:O′, N′)bis(μ2-hexamethylenetetramino-κ2N;N′)silver(I)], {C22H30Ag2N9O6S2}n
  24. Crystal structure of diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-κ4O,O′,N,N′)]zinc(II) dihydrate, C13H18N4O12Zn
  25. The crystal structure of poly [(μ3-N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide-κ3-O:N:N′)-(p-toluenesulfonato-κ2O,O′)silver(I)], C25H27Ag1N4O5S
  26. The crystal structure of 1,2-bis(3-bromophenoxy) ethane, C14H12Br2O2
  27. The crystal structure of 4-(pyren-1-yl)butyl-3-nitrobenzoate, C27H21NO4
  28. Crystal structure of bis[(2-(4-chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ1O) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Cl2N4NiO8
  29. The crystal structure of 1,5-dinitro-2,3,4-trichlorobenzene, C6H1Cl3N2O4
  30. The crystal structure of the solid solution of 3,5-dinitropyrazole and 4-chlorine-3,5-dinitropyrazole, C3H1.24Cl0.76N4O4
  31. The cocrystal structure of 4-nitropyrazole — acetic acid (1/1), C5H7N3O4
  32. The crystal structure of propan-2-one O-(2,4,6-trinitrophenyl) oxime, C9H8N4O7
  33. The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
  34. Crystal structure of (acetic acid-κ1O)-bis(μ2-2-chlorobenzoato-κ2O:O′)-(2-chlorobenzoato-κ1O)-(μ2-hydroxy-κ2O:O)-bis(1,10-phenanthroline-κ2N,N′)dimanganese(II) — methanol (1/1), C48H37Cl3Mn2N4O10
  35. Crystal structure of 3-methyl-2-phenyl-1,8-naphthyridine, C15H12N2
  36. Crystal structure of chlorido-(5-acetyl-2-(5-methylpyridin-2-yl)benzen-1-ido-κ2C,N)-pyridine-κN-palladium(II), C19H17ClN2OPd
  37. Crystal structure of (4-methyl-benzoato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C24H45ClN4NiO7
  38. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) 1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl(potassium, rubidium) — ammonia (1/2), [K0.3Rb0.7(18-crown-6)]Cp*⋅2 NH3, C22H45K0.3N2O6Rb0.7
  39. Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
  40. Crystal structure of (E)-N′-((1,6-dihydropyren-1-yl)methylene)isonicotinohydrazide — methanol (1/1), C24H19N3O2
  41. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ3N,O:O′)-(μ4-hexamethylenetetramino-κ4N:N′:N′′:N′′′)disilver(I)] monohydrate, C12H21Ag2N5O8S2
  42. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 16.10.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2019-0507/html
Scroll to top button