Home Crystal structure of (dibenzyl sulphoxide-κO)dibromido-bis(4-bromobenzyl-κC)tin(IV), C28H26Br4OSSn
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Crystal structure of (dibenzyl sulphoxide-κO)dibromido-bis(4-bromobenzyl-κC)tin(IV), C28H26Br4OSSn

  • See Mun Lee , Kong Mun Lo and Edward R.T. Tiekink ORCID logo EMAIL logo
Published/Copyright: September 9, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 1

Abstract

C28H26Br4OSSn, monoclinic, Cm (no. 8), a = 8.4055(1) Å, b = 26.9988(3) Å, c = 6.4207(1) Å, β = 98.164(1)°, V = 1442.34(3) Å3, Z = 2, Rgt(F) = 0.0174, wRref(F2) = 0.0454, T = 100(2) K.

CCDC no.: 1949173

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:0.13 × 0.07 × 0.03 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:14.4 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:67.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:17692, 2510, 0.040
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2498
N(param)refined:166
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Sn0.46363(3)0.50000.38467(4)0.01593(10)
Br10.41540(7)0.50000.76184(9)0.02340(15)
Br20.15628(7)0.50000.24379(8)0.01954(14)
Br30.02290(6)0.25850(2)0.21959(8)0.02924(13)
S10.84061(18)0.50000.7253(2)0.0188(3)
O10.7397(5)0.50000.5078(7)0.0225(9)
C10.5227(5)0.42751(15)0.2760(7)0.0214(9)
H1A0.55400.43120.13390.026*
H1B0.61830.41530.36990.026*
C20.3954(5)0.38851(14)0.2647(7)0.0185(8)
C30.3060(6)0.37553(15)0.0714(7)0.0207(8)
H30.32160.3932−0.05210.025*
C40.1948(5)0.33718(15)0.0582(7)0.0213(9)
H40.13510.3283−0.07340.026*
C50.1723(5)0.31206(15)0.2396(7)0.0218(9)
C60.2572(6)0.32443(16)0.4326(7)0.0245(9)
H60.24010.30700.55590.029*
C70.3677(6)0.36280(16)0.4433(7)0.0235(9)
H70.42580.37170.57580.028*
C80.9797(5)0.55141(17)0.7211(7)0.0207(9)
H8A1.06870.54830.83910.025*
H8B1.02600.55120.58760.025*
C90.8897(5)0.59888(15)0.7409(7)0.0202(8)
C100.8210(6)0.60822(17)0.9231(7)0.0237(9)
H100.83200.58461.03390.028*
C110.7373(6)0.65153(18)0.9427(8)0.0282(10)
H110.68940.65751.06580.034*
C120.7232(6)0.68634(18)0.7826(9)0.0298(10)
H120.66640.71630.79690.036*
C130.7912(7)0.67772(17)0.6023(8)0.0292(10)
H130.78110.70160.49250.035*
C140.8747(6)0.63376(17)0.5826(7)0.0242(9)
H140.92180.62780.45890.029*

Source of material

The melting point of the compound was measured on a Electrothermal digital melting point apparatus and was uncorrected. The elemental analysis was performed on a Perkin-Elmer EA2400 CHN analyser. The IR spectrum was recorded using a Perkin-Elmer RX1 spectrophotometer as a Nujol mull between KBr plates from 4000 to 400 cm−1. The 1H and 13C{1H} NMR spectra were recorded in CDCl3 solution on a Bruker AVN FT-NMR 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 mmol) and dibenzyl sulfoxide (Aldrich, 0.23 g, 1.0 mmol) were dissolved in chloroform (25 mL) and the mixture was refluxed for 2 h. After filtration, the filtrate was evaporated slowly until colourless crystals were formed. The crystals were filtered, washed with minimum amount of hexane and air-dried. Yield: 0.34 g (40.1%). M.pt: 418–420 K. Anal. Calc. for C28H26Br4OSSn: C 39.62; H 3.09%. Found: C 39.10; H 2.81%. IR (cm−1) 980 (m) ν(S—O), 501 (w) ν(Sn—O). 1H NMR (CDCl3, ppm): δ 3.11 (m, 4H, CH2), 3.92 (s, 4H, SCH2), 6.83–7.18 (m, 8H, BrPh-H), 7.28–7.40 (m, 10H, Ph-H). 13C{1H} NMR (CDCl3, ppm): 35.4 (CH2), 56.2 (SCH2), 119.7, 128.4, 128.8, 121.2, 129.8, 130.2, 131.8, 135.1 (Ph-H).

Experimental details

The H atoms were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The absolute structure was determined based on differences in Friedel pairs.

Comment

Recently, the X-ray crystal structure determination of (4-bromobenzyl)2SnBr2, the organotin precursor in the title compound, (4-bromobenzyl)2SnBr2[O= S(benzyl)2], hereafter (I), became available [6]. In continuation of structural studies of diorgano sulphoxide adducts of organotin derivatives [7], [8], compound (I), was investigated by X-ray crystallography.

The molecular structure of (I) is shown in the figure (70% displacement ellipsoids; unlabelled residues are related by the symmetry operation (i) x, 1 − y, z) and has crystallographic mirror symmetry with the Sn, Br1, Br2, S1 and O1 atoms lying on the mirror plane. The molecule features a penta-coordinated tin centre within a C2Br2O donor set defined by two methylene-carbon, two bromide and sulphoxide-oxygen atoms. The coordination geometry approximates a trigonal-bipyramid with the axial positions occupied by the Br2 and O1 atoms [Br2—Sn—O1 = 179.47(10)°]. This description is quantified in the value of τ = 0.82, compared to τ = 1.0 for an ideal trigonal-bipyramid as opposed to τ = 0.0 for an ideal square-pyramid [9], [10]. There are systematic differences in the magnitudes of the Sn—Br bond lengths relating to their positions in the coordination polyhedron. The axially-bound Br2 atom forms a longer bond [2.6131(7) Å] compared with the equatorially-bound Br1 atom [2.5115(6) Å]. Compared with the Sn—Br bond length [2.5143(2) Å] obtained for 2-fold symmetric (4-bromobenzyl)2SnBr2 [6], only the Sn—Br2 bond length has elongated despite the increase in the coordination number about the tin atom. The sulphoxide-benzyl rings are folded to be disposed over the bromobenzyl rings with the closest intramolecular contact between the residues being a bromobenzyl-methylene-C—H⋯C(benzyl-phenyl) contact [C1—-H1b⋯C14i = 2.74 Å].

There are four notable points of contact between residues in the molecular packing of (I). Thus, a benzyl-C—H⋯Br(tin-bound) contact [C8—H8a⋯Br2ii: H8a⋯Br2ii = 2.91 Å, C8⋯Br2ii = 3.739(4) Å with angle at H8a = 142° for (ii) 1 + x, y, 1 + z] link molecules into a linear, supramolecular chain along [1 0 1]; from symmetry, each molecule participates in four such contacts. Weak bromobenzyl-phenyl-C—H⋯π(benzyl-phenyl) contacts [C4—H4⋯Cg(C9–C14)iii: H4⋯Cg(C9–C14)iii = 2.92 Å, C4⋯Cg(C9–C14)iii = 3.579(5) Å with angle at H4 = 127° for (iii) −1 + x, 1 − y, −1 + z] contribute to the stability of the chain. The connections between the chains are of the type end-on, bromobenzyl-C—Br⋯π(benzyl) [C5—Br3⋯Cg(C2–C7)iv: Br3⋯Cg(C2—C7)iv = 3.5846(18) Å, C5⋯Cg(C2—C7)iv = 5.477(4) Å with angle at Br3 = 171.00(14)° (iv) −1/2 + x, 1/2 − y, z] and, again, there are four such contacts per molecule, so a three-dimensional architecture ensues. The fourth point of contact between atoms is a secondary Sn⋯Br interaction [Sn⋯Br1v = 3.9618(6) Å compared with the sum of the van der Waals radii = 4.02° for (v) x, y, −1 + z] known to be important in crystals of main group elements [11], [12].

A further analysis of the molecular packing was conducted by calculating the Hirshfeld surfaces along with the two-dimensional fingerprint plots (overall and decomposed into individual contacts types) to determine the major types of contacts contributing to the surface. This was performed with Crystal Explorer 17 [13] in accord with established procedures [14]. There are four prominent contributions to the Hirshfeld surface that account for over 97% of all contacts. These are H⋯H [42.4%], Br⋯H/H⋯Br [32.5%], C⋯H/H⋯C [15.4%] and Br⋯C/C⋯Br [6.8%]. The aforementioned Sn⋯Br secondary bonding interaction contributes a mere 0.1% to the overall surface.

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: CrysAlisPRO. 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

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

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. Amin, N. A. B. M.; Hussen, R. S. D.; Lee, S. M.; Halcovitch, N. R.; Jotani, M. M.; Tiekink, E. R. T.: trans-Di-chlorido-bis(dimethyl sulfoxide-κO)bis(4-fluorobenzyl-κC1)-tin(IV): crystal structure and Hirshfeld surface analysis. Acta Crystallogr. E73 (2017) 667–672.10.1107/S2056989017005072Search in Google Scholar

8. Lee, S. M.; Lo, K. M.; Tiekink, E. R. T.: Crystal structure of (dibenzyl sulphoxide-κO)bis(2-chlorobenzyl-κC1)-dichloridotin(IV), C28H26Cl4OSSn. Z. Kristallogr. NCS 234 (2019) 787–789.10.1515/ncrs-2019-0113Search in Google Scholar

9. Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C.: Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane]-copper(II) perchlorate. J. Chem. Soc. Dalton Trans. (1984) 1349–1356.10.1039/DT9840001349Search in Google Scholar

10. Mejia-Rivera, F. J.; Alvarado-Rodríguez, J. G.; Andrade-López, N.; Cruz-Borbolla, J.; Jancik, V.: Intramolecular interactions Sn–D in organotin heterocyclic compounds [{D(C6H4CH2)}SnBr2]. Inorg. Chem. Commun. 97 (2018) 44–48.10.1016/j.inoche.2018.09.006Search in Google Scholar

11. Alcock, N. W.: Secondary bonding to nonmetallic elements. Adv. Inorg. Chem. Radiochem. 15 (1972) 1–58.10.1016/S0065-2792(08)60016-3Search in Google Scholar

12. 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

13. 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

14. 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: 2019-07-29
Accepted: 2019-08-25
Published Online: 2019-09-09
Published in Print: 2019-12-18

©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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  64. Crystal structure of cyclo[tetra(μ2-cyanido)-tetracyanido-bis(1,4,7,10-tetraazacyclododecane-κ4N,N′,N′′,N′′′)dinickel(II)dipalladium(II)] hexahydrate, C24H52N16Ni2O6Pd2
  65. Crystal structure of (dimethyl sulfoxide)-dioxido-[2-hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato κ3N,O,O′]molybdenum(VI), C19H20MoN2O6S
  66. Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5
  67. Crystal structure of chlorido-diphenyl-(isopropyl(propyl)carbamodithioato-κ2S,S′)tin(IV), C19H24ClNS2Sn
  68. The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O
  69. The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
  70. Crystal structure of di(naphthalen-2-yl)sulfane, C20H14S
  71. Crystal structure of 3-acetyl-6-bromo-4-hydroxy-2H-chromen-2-one, C11H7BrO4
  72. Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4
  73. The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
  74. The crystal structure of 1,2-bis((4-methoxyphenyl)ethynyl)benzene, C24H18O2
  75. Crystal structure of a low-temperature (100 K) polymorph of catena-poly[(μ2-4,4′-bipyridine-κ2N,N′)-bis(O,O′-diethyldithiophosphato-κ1S)zinc(II)], C18H28N2O4P2S4Zn
  76. The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
  77. Crystal structure of 3-iodophthalic acid, C8H5IO4
  78. The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
  79. The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
  80. Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
  81. A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n
https://doi.org/10.1515/ncrs-2019-0541
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Articles in the same Issue

  1. 10.1515/ncrs-2020-frontmatter1
  2. The crystal structure of 3,5-dicarboxybenzenaminium perchlorate monohydrate, C8H8ClNO9
  3. The crystal structure of poly[(m4-4-bromoisophthalato-κ4O: O′:O′′:O′′′)zinc(II)], C8H3BrO4Zn
  4. Crystal structure of (E)-2-(2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothioamide, C8H8ClN3O4S
  5. Crystal structure of 1,1′-methylenebis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C11H18F12N4P2
  6. The crystal structure of hexakis(1-isopropyl-1H-imidazole-κ1N)copper(II) dichloride, C36H58Cl2CuN12
  7. Crystal structure of catena-poly[μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dicobalt(II)], C19H10Cl6CoN3O6
  8. Crystal structure of (E)-1-(4-(((E)-2-bromo-6-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15BrN2O2
  9. Crystal structure of ethyl 2-methyl-4-(5-methylthiophen-2-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H21NO3S
  10. The crystal structure of 5-bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine, C7H6BrN5
  11. Crystal structure of Bis(acetato-κ2O,O′)-bis[4-(dimethylamino)pyridine-κN]nickel(II), C18H26N4NiO4
  12. Crystal structure of (E)-3-chloro-2-(((4-chlorophenyl)imino)methyl)phenol, C13H9Cl2NO
  13. The co-crystal structure of (17b)-estra-1,3,5(10)-triene-3,17diol – acetamide (1/1), a Z′ = 4 structure, C20H29NO3
  14. Crystal structure of 3-(3-(pyridin-3-yl)ureido)benzoic acid, C13H11N3O3
  15. The crystal structure of 1,1′-(9-ethyl-9H-carbazole-3,6-diyl)bis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(IV)), C24H27N5F12P2
  16. The crystal structure of 2-bromoisophthalic acid, C8H5BrO4
  17. The crystal structure of 13-ethoxycarbonyl-9-methyl-4-chlor-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene, C14H15ClN2O3S
  18. The crystal structure of (E)-4-((4-(diethylamino)benzylidene)amino)-N,N-diphenylaniline, C29H29N3
  19. Crystal structure of 2-(3-(2-(4-phenylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C27H27N3O2
  20. Crystal structure of 2-ethoxy-6-((E)-((3-(((E)-3-ethoxy-2-hydroxybenzylidene)amino)-2-hydroxypropyl)iminio)methyl)phenolate, C21H26N2O5
  21. The crystal structure of catena-poly(μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dinickel(II)], C19H10Cl6N3NiO6
  22. Crystal structure of hexakis(μ2-azido-κ2N:N)-diazido-κ1N-tetrakis(phenanthroline-κ2N,N′)tetrazinc(II), C48H32N32Zn4
  23. Synthesis and crystal structure of bis{2-bromo-6-(((4-(1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II)–dichloromethane(1/1), C34H32Br2Cl4CoN4O4
  24. Crystal structure of (E)-3-chloro-2-(((4-nitrophenyl)imino)methyl)phenol, C13H9ClN2O3
  25. Crystal structure of aqua-bis(5-bromo-6-methyl-picolinato-κ2N,O)zinc(II) dihydrate, C14H16Br2N2O7Zn
  26. Crystal structure of biaqua(2,2′-bipyridine-4,4′-dicarboxylato-κ2N,N′)(pyridine-2,6-dicarboxylato-κ3O,N,O′)nickel(II) hydrate, C19H15N3NiO10
  27. Synthesis and crystal structure of bis(2-(((4-(1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-fluorophenolato-κ2N,O)zinc(II) - methanol (1/1), C33H32F2N4O4Zn
  28. Crystal structure of tetraaqua-bis(μ2-5-aminoisophthalato-κ3N:O,O′)-bis(4,4′-dipyridylsulfide-κ1N)dizinc(II), C36H34N6O12S2Ni2
  29. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)palladium(II) tetracyanonickelate(II), C14H24N8NiPd
  30. The crystal structure of 3-benzyl-1-((8-(benzyloxy)quinolin-2-yl)methyl)-1H-imidazol-3-ium hexafluorophosphate, C27H24N3OF6P
  31. Crystal structure of 1-(4-chloro-2-hydroxy-5-iodophenyl)ethan-1-one, C8H6ClIO2
  32. Crystal structure of hexaaquamagnesium(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C28H40MgN6O12S2
  33. Crystal structure of the coordination polymer catena-poly[(1,2-di(pyridin-4-yl)ethane-κN)-(μ2-2-nitroisophthalato-κ2O:O′)zinc(II)], C20H17N3O7Zn
  34. Crystal structure of catena-{[tri-aqua-di-sodium bis(2-{[n-butyl(methyl)carbamothioyl]sulfanyl}acetate)]}n, [C16H34N2Na2O7S4]n
  35. The crystal structure of diaqua-bis(μ2-3-((3-acetyl-5-carboxyphenyl)oxidophosphoryl)-5-carboxybenzoato-κ2O:O′)bis(5,5′-dimethyl-2,2′-bipyridine-k2N,N′)zinc(II), C56H46N4O22P2Zn2
  36. Crystal structure of N′,2-bis((E)-2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothiohydrazide, C15H12Cl2N4O2S
  37. Crystal structure of 2-[(1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl]-5-(dodecyloxy)benzen-1-olate, C23H39NO5
  38. Crystal structure of 12-(2-hydroxybenzoyl)benzo[f]pyrido[1,2-a]indole-6,11-dione, C23H13NO4
  39. Crystal structure of chlorido-(4-chloro-6-(p-tolyl)pyrimidine-κ2C,N)-(triphenylphosphane-κP)palladium(II), C29H23Cl2N2PPd
  40. Crystal structure of catena-poly[diaqua-bis(3,4,5,6-tetrabromo-carboxybenzoato-κ1O)-(μ2-4,4′-bipyridine-κ2N:N′)cobalt(II)], C26H14Br8CoN2O10
  41. Crystal structure of catena-poly[dibenzyl-dichlorido-(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′)tin(IV)], C24H22Cl2N2O2Sn
  42. Crystal structure of benzyl-chlorido-(4-chloro-N-[(2-oxidophenyl)methylidene]benzenecarbohydrazonato)-methanol-tin(IV), C22H20Cl2N2O3Sn
  43. Crystal structure of catena-poly[triaqua-(1,3-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(3-nitrophthalato-κ1O)cobalt(II)] — water (2/3), C20H22N5O10.5Co
  44. Crystal structure of (3R,5R,8R,9R,10R,12R,13R,14R)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol, C30H52O3
  45. Crystal structure of 3-(3-(4-carboxyphenyl)ureido)pyridin-1-ium perchlorate, C26H24Cl2N6O14
  46. Crystal structure of 8-hydroxy-2-methylquinolin-1-ium chloride dihydrate, C10H14ClNO3
  47. Crystal structure of (dibenzyl sulphoxide-κO)dibromido-bis(4-bromobenzyl-κC)tin(IV), C28H26Br4OSSn
  48. Crystal structure of bromido-tri(4-chlorophenyl-κ1C)-(ethanol-κ1O)tin(IV) — 4,4′-dimethyl-2,2′-bipyridine (2/1), C52H48Br2Cl6N2O2Sn2
  49. Crystal structure of 2-butyl-6-(ethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione, C18H20N2O2
  50. Crystal structure of (4-chloro-N-[(2-oxido-5-chlorophenyl)methylidene] benzene-carbohydrazonato-κ3N,O,O′)bis(2-fluorobenzyl)tin(IV), C28H20Cl2F2N2O2Sn
  51. Crystal structure of aqua-chlorido-(4-fluorobenzyl-κC)-(N′-(4-methoxy-2-oxidobenzylidene)-3-hydroxy-2-naphthohydrazidato-κ3N,O,O′)tin(IV), C26H22ClFN2O5Sn
  52. Crystal structure of catena-poly[tri(4-chlorophenyl)-(μ2-hydroxido)tin(IV)] – 2-propanol (1/1), C21H21Cl3O2Sn
  53. Crystal structure of bromido-dimethyl-4-tolyl-(triphenylphosphine oxide)tin(IV), C27H28BrOPSn
  54. Crystal structure of 2-(bis(2-hydroxyethyl)ammonio)ethane-1-sulfonate, C6H15NO5S
  55. Crystal structure of bis[triaqua-(μ2-1,2-di(4-pyridyl)ethylene-κ2N:N′)-(4-sulfonatobenzoato-κ2O,O′)zinc(II)], C13H15NO8SZn
  56. Crystal structure of 2-((2-(3-hydroxy-7-methylene-2,3-dihydro-7H-furo[3,2-g]chromen-2-yl)propan-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol – a marmesin derivative, C20H24O10
  57. Crystal structure of octa(4-chlorobenzyl)-dichlorido-bis(μ2-methanolato)-bis(μ3-oxo)-tetratin(IV), C58H54Cl10O4Sn4
  58. Crystal structure of iodido-triphenyl-(triphenylphosphine oxide)tin(IV), C36H30IOPSn
  59. Crystal structure of dichlorido-bis(4-methylphenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C50H44As2Cl2O2Sn
  60. Crystal structure of 4-benzyl-1-oxo-N-phenethyl-1H-[1,4]oxazino [4,3-b]indazole-3-carboxamide, C26H21N3O3
  61. Crystal structure of bis{(N-[(5-chloro-2-oxidophenyl)methylidene]-2-hydroxybenzenecarbohydrazonato)-dioxo-molybdenum(VI)}(μ2-4,4′-bipyridine), C38H26Cl2Mo2N6O10
  62. Crystal structure of dichlorido-octamethyl-bis(μ3-oxido)-bis(μ2-2-(phenylamino)ethanolato-κ2O:O)tetratin(IV), C24H44Cl2N2O4Sn4
  63. The crystal structure of 1-(2-(2-(imidazo[1,5-a]pyridine-4-ium)ethoxy)ethyl)-imidazo[1,5-a]pyridine-4-ium bis(hexafluorophosphate) — acetonitrile (1/1), C18H20ON4F12P2
  64. Crystal structure of cyclo[tetra(μ2-cyanido)-tetracyanido-bis(1,4,7,10-tetraazacyclododecane-κ4N,N′,N′′,N′′′)dinickel(II)dipalladium(II)] hexahydrate, C24H52N16Ni2O6Pd2
  65. Crystal structure of (dimethyl sulfoxide)-dioxido-[2-hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato κ3N,O,O′]molybdenum(VI), C19H20MoN2O6S
  66. Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5
  67. Crystal structure of chlorido-diphenyl-(isopropyl(propyl)carbamodithioato-κ2S,S′)tin(IV), C19H24ClNS2Sn
  68. The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O
  69. The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
  70. Crystal structure of di(naphthalen-2-yl)sulfane, C20H14S
  71. Crystal structure of 3-acetyl-6-bromo-4-hydroxy-2H-chromen-2-one, C11H7BrO4
  72. Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4
  73. The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
  74. The crystal structure of 1,2-bis((4-methoxyphenyl)ethynyl)benzene, C24H18O2
  75. Crystal structure of a low-temperature (100 K) polymorph of catena-poly[(μ2-4,4′-bipyridine-κ2N,N′)-bis(O,O′-diethyldithiophosphato-κ1S)zinc(II)], C18H28N2O4P2S4Zn
  76. The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
  77. Crystal structure of 3-iodophthalic acid, C8H5IO4
  78. The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
  79. The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
  80. Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
  81. A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n
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