Home Crystal structure of chlorido-4-fluorobenzyl-bis(2-methylquinolin-8-olato-κ2N,O)tin(IV), C27H22ClFN2O2Sn
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Crystal structure of chlorido-4-fluorobenzyl-bis(2-methylquinolin-8-olato-κ2N,O)tin(IV), C27H22ClFN2O2Sn

  • See Mun Lee , Kong Mun Lo and Edward R.T. Tiekink ORCID logo EMAIL logo
Published/Copyright: April 22, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 4

Abstract

C27H22ClFN2O2Sn, tetragonal, P41 (no. 76), a = 9.38970(10) Å, c = 26.2753(4) Å, V = 2316.60(6) Å3, Z = 4, Rgt(F) = 0.0141, wRref(F2) = 0.0381, T = 293(2) K.

CCDC no.: 1903610

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:0.23 × 0.12 × 0.07 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.26 mm−1
Diffractometer, scan mode:CCD, φ and ω
θmax, completeness:28.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:23534, 5789, 0.015
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5771
N(param)refined:310
Programs:Bruker [1], SHELX [2], [3], [4], WinGX/ORTEP [5]
Table 2:

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

AtomxyzUiso*/Ueq
Sn0.56825(2)0.96184(2)0.47956(2)0.01355(4)
Cl10.66301(6)1.19480(6)0.49951(2)0.02051(10)
F11.06407(19)0.4888(2)0.54974(9)0.0420(5)
O10.63761(17)0.90109(17)0.54997(6)0.0160(3)
O20.46540(18)1.03242(17)0.41571(6)0.0179(3)
N10.4625(2)0.74188(19)0.49075(7)0.0155(4)
N20.3471(2)1.04282(19)0.50961(7)0.0138(3)
C10.6127(2)0.7666(2)0.56379(8)0.0154(4)
C20.5194(2)0.6808(2)0.53362(8)0.0151(4)
C30.3767(2)0.6666(2)0.46073(9)0.0179(4)
C40.3426(2)0.5237(2)0.47276(9)0.0204(5)
H40.2823510.4721600.4515540.025*
C50.3977(3)0.4611(2)0.51535(9)0.0201(4)
H50.3744240.3673300.5231250.024*
C60.4900(2)0.5383(2)0.54762(8)0.0174(4)
C70.5531(3)0.4821(3)0.59211(9)0.0213(4)
H70.5350540.3885060.6017610.026*
C80.6409(3)0.5661(3)0.62099(9)0.0211(4)
H80.6818010.5289170.6503640.025*
C90.6705(2)0.7081(2)0.60695(9)0.0187(4)
H90.7301560.7629020.6272950.022*
C100.3149(3)0.7365(3)0.41464(10)0.0254(5)
H10A0.2488880.8090840.4249750.038*
H10B0.2661250.6667200.3944220.038*
H10C0.3899120.7787440.3949350.038*
C110.3386(2)1.0940(2)0.42062(8)0.0155(4)
C120.2730(2)1.0992(2)0.46928(8)0.0144(4)
C130.2888(2)1.0428(2)0.55587(8)0.0169(4)
C140.1508(3)1.0992(2)0.56331(9)0.0198(4)
H140.1103561.0966640.5956050.024*
C150.0760(3)1.1570(3)0.52406(9)0.0211(5)
H15−0.0142701.1945440.5297280.025*
C160.1354(2)1.1601(2)0.47481(10)0.0182(4)
C170.0648(3)1.2160(3)0.43187(10)0.0220(5)
H17−0.0258461.2550170.4350700.026*
C180.1310(3)1.2123(3)0.38522(9)0.0217(5)
H180.0849931.2502090.3569640.026*
C190.2674(2)1.1520(2)0.37952(9)0.0184(4)
H190.3102181.1512390.3476020.022*
C200.3667(3)0.9809(3)0.60017(9)0.0240(5)
H20A0.3754040.8797470.5957750.036*
H20B0.3150531.0004560.6309020.036*
H20C0.4599071.0225750.6023070.036*
C210.7359(3)0.8699(3)0.43242(9)0.0222(5)
H21A0.6933910.8220770.4034340.027*
H21B0.7967450.9453630.4196660.027*
C220.8239(3)0.7655(2)0.46209(9)0.0206(4)
C230.9402(3)0.8128(3)0.49020(10)0.0263(5)
H230.9636300.9090280.4892960.032*
C241.0227(3)0.7212(3)0.51963(11)0.0299(6)
H241.1006150.7546650.5379360.036*
C250.9854(3)0.5800(3)0.52075(11)0.0275(5)
C260.8714(3)0.5277(3)0.49365(11)0.0278(5)
H260.8485020.4314160.4950570.033*
C270.7910(3)0.6204(3)0.46419(10)0.0246(5)
H270.7142760.5854870.4456060.029*

Source of material

Instrumentation: The elemental analysis was performed on a Perkin-Elmer EA2400 CHN analyser. The IR spectrum was recorded using a Perkin-Elmer RX1 spectrophotometer in a Nujol mull between KBr plates. The 1H and 13C{1H} NMR spectra were recorded in CDCl3 solution on a Bruker AVN FT-NMR spectrometer with chemical shifts relative to Me4Si for 1H and CDCl3 for 13C{1H}.

Synthesis: Di(4-fluorobenzyl)tin dichloride was prepared from the direct synthesis method using tin powder (Sigma-Aldrich) and 4-fluorobenzyl chloride (Sigma-Aldrich) in toluene [6]. The ligand, 2-methyl-8-hydroxyquinoline (Sigma-Aldrich; 0.31 g, 2.0 mmol) and di(4-fluorobenzyl)tin dichloride (0.41 g, 1.0 mmol) were heated in 95% ethanol (50 mL) for 1 h. After filtration, the filtrate was evaporated slowly until colourless crystals were formed. Yield: 0.35 g (60%). M. pt: 479−481 K. Calcd for C27H22ClFN2O2Sn: C 55.91; H 3.79; N 4.83%. Found: C 55.57; H 3.18; N 5.25%. IR (cm−1) 407 (w) ν(Sn—N), 528 (m) ν(Sn—O), 1108 (s) ν(C—O), 1578 (s) ν(C=N). 1H NMR (CDCl3, ppm): δ 6.67−6.76 (m, 4H, Ph-H), 3.15 (s, 2H, Ph-CH2), 7.01–8.79 (m, 10H, oxin-H), 2.51 (s, 6H, oxin-CH3). 13{1H}C NMR (CDCl3, ppm): δ 24.3 (CH3), 37.4 (CH2), 138.9, 128.0, 127.4, 123.8 (C-Ph), 113.9, 121.0, 121.8, 129.5, 130.6, 139.8, 140.4, 143.4, 155.1 (C-oxin).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.93−0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). Owing to poor agreement, the (0 0 4̄) reflection was omitted from the final cycles of refinement. The sample was refined as a two-component inversion twin with the minor component refining to 0.074(12).

Comment

The chelating ability of 8-hydroxyquinoline (oxine) and its derivatives has resulted in the formation of a large number of metal-oxine complexes [7]. These derivatives of 8-hydroxyquinoline and their metal complexes are known to exhibit various biological activities [7], [8]. In our efforts to synthesise biologically active diorganotin-oxine complexes, the reaction of dibenzyltin dichlorides with various 8-hydroxyquinoline derivatives were performed. In general, the reaction would be expected to form product of the type Bz2SnCl(ox) or Bz2Sn(ox)2 [Bz = benzyl; ox = 8-hydroxyquinolinyl derivative] by replacing either one of both chloride atoms of the diorganotin precursor [9], [10]. In the present study, where a 2:1 reaction of 2-methyl-8-hydroxyquinoline and di(4-fluorobenzyl)tin dichloride was performed, it was found that a mono(4-fluorobenzyl)tin compound was obtained as the predominant product.

The molecular structure is shown in the figure (70% displacement ellipsoids) and reveals the tin atom to be bis-N,O-chelated by two 2-methyl-8-hydroxyquinolinato ligands, one chlorido ligand and the 4-Bz-C atom to result in a CClN2O2 donor set. The coordination geometry approximates an octahedron in which the oxygen atoms are mutually arranged in trans position [O1—Sn—O2 = 169.61(6)°] and the nitrogen atoms are cis to each other [N1—Sn—N2 = 82.33(6)°]. The narrowest angle subtended at the tin atom is the O2—Sn—N2 chelate angle [75.73(6)°] while the widest angle is the aforementioned O1—Sn—O2 angle. Being mutually trans, the Sn—O1 and Sn—O2 bond lengths are experimentally equivalent [2.0426(16) and 2.0462(17) Å, respectively] but, there are systematic variations in the Sn—N bond lengths. Thus, the Sn—N1 bond length [2.3105(19) Å] is shorter than the Sn—N2 bond [2.3480(18) Å] which correlates with the N2 atom being trans to the benzyl-C21 atom [Sn—C1 = 2.181(2) Å]. The five-membered chelate rings adopt distinct conformations. The O1-chelate ring is best described as being an envelope with the tin atom lying 0.304(4) Å above the plane defined by the four remaining atoms of the ring [r.m.s. deviation = 0.005 Å]. By contrast, the O2-chelate ring is planar with the r.m.s. deviation of the five fitted atoms being 0.023 Å; the maximum deviation from the least-squares plane is 0.032(1) Å for the O2 atom. The dihedral angle between the best planes through the chelate rings is 84.48(5)°, consistent with an orthogonal relationship. Finally, the benzyl-ring is approximately folded towards the O1-chelate ring as seen in the dihedral angle of 24.33(11)° between them; the separation between the ring centroids of the respective rings is 3.5973(14) Å.

In the crystal, a combination of weak non-covalent interactions assemble the molecules into a three-dimensional network architecture. Thus, oxinate-C—H⋯O(oxinate) [C18—H18⋯O1i: H18⋯O1i = 2.52 Å, C18⋯O1i = 3.415(3) Å with angle at H18 = 163° for symmetry operation i: −1 + y, 2 −x, −1/4 + z], benzyl-C—H⋯Cl [C26—H26⋯Cl1ii: H26⋯Cl1ii = 2.83 Å, C26⋯Cl1ii = 3.691(3) Å, angle at H26 = 155° for ii: x, −1 + y, z] and oxinate-C—H⋯π(NC5-oxinate) [C5—H5⋯π(N2, C12–C16)ii: H5⋯π(N2,C12–C16)ii = 2.94 Å, C5⋯π(N2,C12–C16)ii = 3.812(2) Å with angle at H5 = 156°] are readily identified points of contact between molecules.

There are two other structures in the literature that resemble that described herein, i.e. with general formula RSn(oxine)2Cl. In each of the R = n-Bu [11] and R = Bz [12] structures, very similar coordination geometries are noted.

Acknowledgements

Sunway University is thanked for supporting studies in organotin chemistry.

References

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Received: 2019-02-20
Accepted: 2019-03-16
Published Online: 2019-04-22
Published in Print: 2019-06-26

© 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.

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  58. Crystal structure of dichlorido(pyridine-κN)(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N2,N1,N6)nickel(II), C23H17Cl2N7Ni
  59. Redetermination of the crystal structure of tetrakis(4-chlorobenzyl)tin(IV), C28H24Cl4Sn
  60. The crystal structure of 2,6-bis(pyridin-1-ium-3-ylmethyl)hexahydro-4,8-ethenopyrrolo-[3,4-f] isoindole-1,3,5,7-tetrone tetrachloridocuprate(II) monohydrate, C24H24Cl4CuN4O5
  61. Crystal structure of cyclo-[octaaqua-tetrakis(μ2-5,5′-(1H-imidazole-4,5-diyl)bis(tetrazol-2-ido)-κ4N,N′,N′′,N′′′)tetramagnesium(II)], C20H24N40O8Mg4
  62. The crystal structure of a matrine derivative, 13-(4-Cl-pyrrole)-matrine, C18H26ClN4O
  63. Crystal structure of (dibenzyl sulphoxide-κO)bis(2-chlorobenzyl-κC1)dichloridotin(IV), C28H26Cl4OSSn
  64. Crystal structure of catena-poly[(μ2-azido-κ2N:N)(μ2-4-cyanobenzoato-κ2O:O′)-(μ2-methanol-κ2O:O)copper(II)], C9H8CuN4O3
  65. Crystal structure of 1,1′-dibenzyl-3,3′-dicyano-1,1′,4,4′-tetrahydro-4,4′-bipyridine, C26H22N4
  66. Crystal structure of (2-bromobenzyl)((1-bromonaphthalen-2-yl)methyl)sulfane, C18H14Br2S
  67. Crystal structure of 2-(4-ammoniocyclohexyl)-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium 2-[(2-carboxylatophenyl)disulfanyl]benzoate dihydrate, [C18H22N4][C14H8O4S2] ⋅ 2H2O
  68. Crystal structure of (E)-N-((3R,5S,10S, 13S,14S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-2-methylbut-2-enamide – water – methanol (1/1/1), C29H54N2O3
  69. Crystal structure of methyl 2-(4-(3-(2,4-difluorophenyl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C21H15F2N3O2
  70. Crystal structure of poly[triaqua-(μ4-benzene-1,3,5-tricarboxylato-κ5O1,O2:O3:O4:O5)-(μ2-5-(3-pyridyl)tetrazolato-κ2N1:N3)dizinc(II)], C15H13N5O9Zn2
  71. Crystal structure of N-(3-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
  72. Crystal structure of poly[(μ2-1,3-bis(imidazol-1-ylmethyl)benzene-κ2N:N′)(nitrato-κ1O)cadmium(II)] — water (2/1), C28H32CdN10O7
  73. Crystal structure of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C8H7N3S
  74. Crystal structure of benzyltrichloridobis(1H-pyrazole-κ2N)tin(IV), C13H15Cl3N4Sn
  75. Crystal structure of chlorido-4-fluorobenzyl-bis(2-methylquinolin-8-olato-κ2N,O)tin(IV), C27H22ClFN2O2Sn
  76. Crystal structure of tetrakis(O,O′-diisopropyldithiophosphato-κ2S,S′)-(μ2-1,2-bis(4-pyridylmethylene)hydrazine-κ2N:N′)zinc(II), C36H66N4O8P4S8Zn2
  77. Crystal structure of tetrabutylammonium 4,4-oxydibenzoate – boric acid – water (1/2/6) C46H98B2N2O17
  78. Redetermination of the crystal structure of catena-poly[[tribenzyltin(IV)]-(μ2-pyridine-4-carboxylato-κ2N:O)], C27H25NO2Sn
  79. The synthysis and crystal structure of cyclohexyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C18H15N3Cl2F6O3S
  80. The crystal structure of 5,7-bis(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one, C19H18O6
  81. Synthesis and crystal structure of (±)-Ethyl 5′-(difluoromethyl)-2-oxo-4′,5′-dihydrospiro[indoline-3,3′-pyrazole]-4′-carboxylate, C14H13F2N3O3
https://doi.org/10.1515/ncrs-2019-0130
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-5-fluorophenol, C14H13FN2O
  3. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-4,6-dichlorophenol, C14H12Cl2N2O
  4. The crystal structure of (E)-1-(4-methoxyphenyl)-3-(2-nitrophenyl)triaz-1-ene C8H8N2O4
  5. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(ethylamino)-2′,7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one—methanol (1:1), C32H30N5O2Br ⋅ CH4O
  6. Crystal structure of 2,4-pentanedione bis(2,4-dinitrophenylhydrazone), C17H16N8O8
  7. Crystal structure of sodium morpholine-4-carbodithioate, (C5H12NNaO3S2)
  8. Crystal structure of 1,1′-(hexane-1,6-diyl)bis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorido phosphate), C16H28F12N4P2
  9. Crystal structure of 5-(4-chlorophenyl)-3-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, C21H16ClFN2
  10. Crystal structure of catena-poly[diaqua-bis(3-carboxy-5-methoxybenzoato-κO)-(1,2-bis(imidazol-1-yl)ethane-κ2N:N′)cobalt(II)], C26H28CoN4O12, [Co(C9H6O5)2(H2O)2(C8H10N4)]
  11. The crystal structure of 3-cyclohexyl-1,5-dioxaspiro[5.5]undecane-2,4-dione, C15H22O4
  12. Crystal structure of (2,4-dimethoxybenzyl)triphenylphosphonium trifluoroacetate — trifluoroacetic acid (1/1), C31H27F6O6P
  13. Crystal structure of 4-tert-butyl-1-(2,6-dimethylphenyl)-1H-1,2,3-triazole, C14H19N3
  14. Crystal structure of 1,1′-methylenebis(4-tert-butylpyridinium) tetrachloridocobaltate(II) – dichloromethane (1:1), C20H30Cl6CoN2
  15. Crystal structure of (4,4′-(ethane-1,2-diylbis((nitrilo)(2-furylmethylylidene)))bis(3-methyl-1-phenyl-1H-pyrazol-5-olato-κ4N,N′,O,O′))-nickel(II)), C32H26N6NiO4
  16. Synthesis and crystal structure of bis{((E)-((4-((E)-1-(benzyloxyimino)ethyl)phenyl)imino)methyl)-2-phenolato-κ2N,O}copper(II), C44H38CuN4O4
  17. Crystal structure of catena-poly[diaqua-bis(3,5-dichloropyridine-4-carboxylato-κ1O)-bis(μ2-4,4′-bipyridine-κ2N:N′)cobalt(II)], C22H16Cl4CoN4O6
  18. The crystal structure of 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro-3,5-dinitrophenyl)diazene 1-oxide, C12H4Cl2N6O9
  19. The crystal structure of 3-(1H-benzo[d]imidazol-2-yl)-7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydroquinolin — dimethylsulfoxide (1/1), C21H19ClFN3O2S
  20. The crystal structure of dichlorido-bis(1-butyl-1H-imidazole-κN)zinc(II), C14H24Cl2ZnN4
  21. (Z)-N-tert-butyl-1-(2-(3,5-dichlorobenzamido)phenyl) methanimine oxide, C18H18Cl2N2O2
  22. Crystal structure of diaqua-bis(3-carboxy-5-bromoisophthalato-κO)-bis(1-(3-(1H-benzo[d]imidazol-1-yl)propyl)-1H-benzo[d]imidazol-3-ium-κN)nickel(II) bis(3-carboxy-5-bromoisophthalate), C66H54Br4N8NiO18
  23. Crystal structure of poly[aqua(μ2-5-methoxyisophthalato-κ2O,O′:O′′)-(1,2-bis(imidazol-1′-yl)ethane-κ2N:N′)cobalt(II), C34H36Co2N8O12
  24. Crystal structure of poly[diaqua-bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′)manganese(II)] terephthalate tetrahydrate, MnC32H38N10O10
  25. Crystal structure of the fluorescent fipronil derivative 5,5′-(methylenebis(azanediyl))bis(1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile), C25H6N8O2Cl4F12S2
  26. Crystal structure of the phosphorescent complex diethyldithiophosphonato-κ2S,S′-bis(2-phenylpyridinato-κ2C,N)iridium(III), C26H26N2O2PS2Ir
  27. The crystal structure of 4,10-diethoxy-6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocine, C18H18O5
  28. Crystal structure of dichlorido-bis(N-benzyl-2-(quinolin-8-yloxy)acetamide-κ2N,O)copper(II) — ethyl acetate (1/1), C38H36N4O6Cl2Cu
  29. Synthesis and crystal structure of bis{4-methyl-2-((E)-((4-((E)-1-(benzyloxyimino)ethyl)phenyl)imino)methyl)phenolato-κ3N,O,O}copper(II), C92H84Cu2N8O8
  30. The crystal structure of 1,3,5-trinitro-4,6-diazidobenzene, C6HN9O6
  31. Crystal structure 1-cinnamyl-2-((Z)-styryl)-1H-benzo[d]imidazole — methanol (1/1), C24H20N2 ⋅ CH4O
  32. The crystal structure of poly[m2-aqua-tetraaqua-bis(m9-4-formylbenzene-1,3-disulfonato)tetrasodium(I) hydrate, C14H18O19S4Na4
  33. Crystal structure of 2-((2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidin-1-ium trifluoroacetate, [C17H17F6N2O][C2F3O2]
  34. The crystal structure of bis(ferrocenecarboxylato-κ2O,O′)bis[4-(dimethylamino)pyridine-κN]copper(II) — acetonitrile(1/2), C40H44CuO4Fe2N6
  35. Crystal structure of poly[di-μ2-aqua)-diaqua-bis(μ6-4,4′,4′′-(benzene-1,3,5-triyltris(oxy))tribenzoato-κ6O1:O2:O3:O3:O5:O6)tricadmium(II)] dihydrate, C54H42Cd3O24
  36. The crystal structure of dichlorido(1,3-bis(2,6-diisopropyl-phenyl)-1H-3λ4-imidazol-2-yl)(3-phenyl-pyridine-κN)palladium(IV), C38H45N3Cl2Pd
  37. The crystal structure of 2-chloro-4-(prop-2-yn-1-yloxy)-6-phenyl-1,3,5-triazine, C12H8ClN3O
  38. The crystal structure of 2,6-di-tert-butyl-4-(phenyl(phenylsulfonyl)methyl)phenol, C27H32O3S
  39. Crystal structure of bis{μ2-bis{(((((1-methoxyimino)ethyl)phenyl)imino)methyl)-2-phenolato-κ3N,O:O}copper(II)}, C68H68Cu2N8O8
  40. Crystal structure of catena-poly[tetraaqua-bis(μ2-2-(4-carboxylatophenoxy)benzoato-κ2O:O′)-pentakis(pyridine-κ1N)dinickel(II)], C53H47N5Ni2O13
  41. Synthesis and crystal structure of 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(3-methoxy-benzylamino)-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile, C20H12N4Cl2F6O2S
  42. Redetermination of the crystal structure of bis(μ2-di-ethyldithiocarbamato-κ3S,S′:S;κ3S:S: S′)-hexacarbonyl-di-rhenium(I), C16H20N2O6Re2S4
  43. The crystal structure of (E)-N′-((2-hydroxynaphthalen-1-yl)methylene)-2-phenylacetohydrazide, C19H16O2N2
  44. Crystal structure of 6-hydroxy-4,8,11b-trimethyltetradecayhdro-8,11-epoxy-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid – methanol (1/1), C20H30O4
  45. The crystal structure of aqua-bis(3-acetyl-2-oxo-2H-chromen-4-olato-κ2O,O′)zinc(II) monohydrate, C22H18O10Zn
  46. Crystal structure of poly[bis(μ2-4-bromoisophthalate-κ2O:O′)-tris(μ2-1-(3-((1H-1,2,4-triazol-1-yl)methyl)benzyl)-1H-1,2,4-triazole-κ2N:N′)dicobalt(II)] monohydrate, C26H23CoN9O5Br
  47. A cyclic I102− anion in the layered crystal structure of theophyllinium pentaiodide, C7H9I5N4O2
  48. Crystal structure of catena-poly[diaqua-bis(μ2-4-((4-(pyridin-2-ylmethoxy)phenyl)diazenyl)benzoato-κ3O,O′:N)cadmium(III)], Cd(C19H14O3N3)2(H2O)
  49. Crystal structure of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-dimethyldithiophosphato-κS)-zinc(II)], {C14H20N2O4P2S4Zn}n
  50. Crystal structure of 3-amino-2-hydroxy-6-methoxybenzamide hydrate, C16H22N4O7
  51. Crystal structure of hemikis(cyclohexane-1,4-diammonium) (pyridine-2-carboxylate), [C6H16N2]0.5[C6H4NO2]
  52. Crystal structure of 2-chloro-4-(prop-2-yn-1-yloxy)-6-(thiophen-2-yl)-1,3,5-triazine, C10H6ClN3OS
  53. The crystal structure of 3-butyl-1-methyl-1H-imidazol-3-ium catena-poly[tris(μ2-bromido-κ2Br:Br)lead(II)], C8H15Br3N2Pb
  54. Crystal structure of 3-(5-amino-1H-1,2,4-triazol-3-yl)-1-(piperidin-1-yl)propan-1-one, C10H17N5O
  55. Crystal structure of aqua-2,2′,2′′-(((nitrilo-κN-tris(ethane-2,1-diyl))tris(azanylylidene-κ3N′,N′′,N′′′))tris(methanylylidene))tris(4-chlorophenolato-κ3O,O′,O′′)neodymium(III), C27H26Cl3N4NdO4
  56. Crystal structure of dichlorido-(μ2-2,2′-(diazene-1,2-diyl)bis(benzen-1-ido)-κ2C:C′)dimercury(II), C12H8Cl2Hg2N2
  57. Crystal structure of (3E,5E)-3,5-bis(4-cyanobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one, C27H18FN3O3S
  58. Crystal structure of dichlorido(pyridine-κN)(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N2,N1,N6)nickel(II), C23H17Cl2N7Ni
  59. Redetermination of the crystal structure of tetrakis(4-chlorobenzyl)tin(IV), C28H24Cl4Sn
  60. The crystal structure of 2,6-bis(pyridin-1-ium-3-ylmethyl)hexahydro-4,8-ethenopyrrolo-[3,4-f] isoindole-1,3,5,7-tetrone tetrachloridocuprate(II) monohydrate, C24H24Cl4CuN4O5
  61. Crystal structure of cyclo-[octaaqua-tetrakis(μ2-5,5′-(1H-imidazole-4,5-diyl)bis(tetrazol-2-ido)-κ4N,N′,N′′,N′′′)tetramagnesium(II)], C20H24N40O8Mg4
  62. The crystal structure of a matrine derivative, 13-(4-Cl-pyrrole)-matrine, C18H26ClN4O
  63. Crystal structure of (dibenzyl sulphoxide-κO)bis(2-chlorobenzyl-κC1)dichloridotin(IV), C28H26Cl4OSSn
  64. Crystal structure of catena-poly[(μ2-azido-κ2N:N)(μ2-4-cyanobenzoato-κ2O:O′)-(μ2-methanol-κ2O:O)copper(II)], C9H8CuN4O3
  65. Crystal structure of 1,1′-dibenzyl-3,3′-dicyano-1,1′,4,4′-tetrahydro-4,4′-bipyridine, C26H22N4
  66. Crystal structure of (2-bromobenzyl)((1-bromonaphthalen-2-yl)methyl)sulfane, C18H14Br2S
  67. Crystal structure of 2-(4-ammoniocyclohexyl)-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium 2-[(2-carboxylatophenyl)disulfanyl]benzoate dihydrate, [C18H22N4][C14H8O4S2] ⋅ 2H2O
  68. Crystal structure of (E)-N-((3R,5S,10S, 13S,14S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-2-methylbut-2-enamide – water – methanol (1/1/1), C29H54N2O3
  69. Crystal structure of methyl 2-(4-(3-(2,4-difluorophenyl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C21H15F2N3O2
  70. Crystal structure of poly[triaqua-(μ4-benzene-1,3,5-tricarboxylato-κ5O1,O2:O3:O4:O5)-(μ2-5-(3-pyridyl)tetrazolato-κ2N1:N3)dizinc(II)], C15H13N5O9Zn2
  71. Crystal structure of N-(3-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
  72. Crystal structure of poly[(μ2-1,3-bis(imidazol-1-ylmethyl)benzene-κ2N:N′)(nitrato-κ1O)cadmium(II)] — water (2/1), C28H32CdN10O7
  73. Crystal structure of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C8H7N3S
  74. Crystal structure of benzyltrichloridobis(1H-pyrazole-κ2N)tin(IV), C13H15Cl3N4Sn
  75. Crystal structure of chlorido-4-fluorobenzyl-bis(2-methylquinolin-8-olato-κ2N,O)tin(IV), C27H22ClFN2O2Sn
  76. Crystal structure of tetrakis(O,O′-diisopropyldithiophosphato-κ2S,S′)-(μ2-1,2-bis(4-pyridylmethylene)hydrazine-κ2N:N′)zinc(II), C36H66N4O8P4S8Zn2
  77. Crystal structure of tetrabutylammonium 4,4-oxydibenzoate – boric acid – water (1/2/6) C46H98B2N2O17
  78. Redetermination of the crystal structure of catena-poly[[tribenzyltin(IV)]-(μ2-pyridine-4-carboxylato-κ2N:O)], C27H25NO2Sn
  79. The synthysis and crystal structure of cyclohexyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C18H15N3Cl2F6O3S
  80. The crystal structure of 5,7-bis(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one, C19H18O6
  81. Synthesis and crystal structure of (±)-Ethyl 5′-(difluoromethyl)-2-oxo-4′,5′-dihydrospiro[indoline-3,3′-pyrazole]-4′-carboxylate, C14H13F2N3O3
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