Home Physical Sciences Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5
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Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5

  • Kong Mun Lo , See Mun Lee and Edward R.T. Tiekink ORCID logo EMAIL logo
Published/Copyright: October 11, 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

C14H25CuNO5, triclinic, P1̄ (no. 2), a = 7.7319(3) Å, b = 9.9198(5) Å, c = 11.6827(5) Å, α = 81.866(4)°, β = 75.576(4)°, γ = 74.562(4)°, V = 833.78(7) Å3, Z = 2, Rgt(F) = 0.0287, wRref(F2) = 0.0807, T = 100(2) K.

CCDC no.: 1953790

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:Blue prism
Size:0.20 × 0.15 × 0.05 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.33 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:25.2°, >99%
N(hkl)measured, N(hkl)unique, Rint:6693, 2993, 0.020
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2850
N(param)refined:199
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Cu0.56895(3)0.51741(3)0.76281(2)0.01278(11)
O10.7586(2)0.44364(16)0.61990(12)0.0138(3)
O20.6933(2)0.35962(16)0.86834(12)0.0128(3)
O30.4413(2)0.67769(16)0.66269(13)0.0138(3)
O40.7137(2)0.64086(16)0.80112(13)0.0147(3)
O50.3553(2)0.58506(17)0.90843(13)0.0143(3)
H5O0.362(4)0.604(3)0.9729(13)0.021*
N10.3764(2)0.40014(19)0.74762(15)0.0125(4)
C10.8800(3)0.3304(2)0.61609(19)0.0139(4)
C20.9146(3)0.2362(2)0.71505(19)0.0157(5)
H21.0068580.1518330.6998580.019*
C30.8259(3)0.2559(2)0.83238(19)0.0134(4)
C40.9971(3)0.2949(3)0.49525(19)0.0187(5)
H4A0.9175390.2987970.4407630.028*
H4B1.0766970.2002350.5009690.028*
H4C1.0731270.3626320.4654280.028*
C50.8881(3)0.1479(2)0.9273(2)0.0198(5)
H5A0.9437190.1894360.9759650.030*
H5B0.9790900.0678260.8903090.030*
H5C0.7821310.1160780.9773870.030*
C60.4456(3)0.8044(2)0.66060(18)0.0148(4)
C70.5564(3)0.8541(2)0.7141(2)0.0187(5)
H70.5442120.9526590.7065240.022*
C80.6836(3)0.7722(2)0.77759(19)0.0155(5)
C90.3184(3)0.9088(2)0.5933(2)0.0223(5)
H9A0.3471150.8848560.5109660.033*
H9B0.3346571.0031910.5946650.033*
H9C0.1906440.9063640.6303680.033*
C100.7988(4)0.8448(3)0.8233(2)0.0244(5)
H10A0.7631330.8408370.9101040.037*
H10B0.7789270.9429710.7909570.037*
H10C0.9291830.7975750.7986020.037*
C110.2038(3)0.5221(2)0.92577(19)0.0160(5)
H11A0.0876720.5881870.9603200.019*
H11B0.2209290.4362830.9805970.019*
C120.1966(3)0.4859(2)0.80598(19)0.0148(4)
H12A0.1007750.4332550.8158970.018*
H12B0.1630030.5732480.7553720.018*
C130.4072(3)0.2570(2)0.8052(2)0.0187(5)
H13A0.3072560.2152990.8017580.028*
H13B0.4100270.2599340.8882040.028*
H13C0.5247750.2003270.7641100.028*
C140.3749(3)0.3929(3)0.62278(19)0.0187(5)
H14A0.4921500.3339950.5835430.028*
H14B0.3574400.4875260.5824960.028*
H14C0.2739520.3522780.6192820.028*

Source of material

All chemicals and solvents were used as purchased without further purification. The melting point of the complex was measured on a Mel-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.

Bis(acetylacetonato)copper(II) was synthesized according to the literature method [5]. Bis(acetylacetonato)copper(II) (0.26 g, 1 mmol) and N,N-dimethylaminoethanol (Sigma-Aldrich, 0.18 g, 2 mmol) were dissolved in ethanol (25 mL) and refluxed for 3 h. The filtrate was evaporated until a light-blue precipitate was obtained. The precipitate was washed with n-hexane and recrystallised from its methanol solution. Light-blue crystals were obtained upon slow evaporation of the filtrate. Yield: 0.28 g (34%). M.pt: >573 K. IR (cm−1) 1576 (s) ν(C—N), 1521 (m) ν(C—O), 1066 (s) ν(C—O), 1017 (m) ν(C—O).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The O-bound H-atom was located from difference Fourier maps and then refined with O—H = 0.84 ± 0.01 Å, and with Uiso(H) = 1.5Ueq(O).

Comment

Bis(acetylacetonato)copper(II), Cu(acac)2, and derivatives have been long known to form stable 5- and 6-coordinate complexes when also complexed with monodentate nitrogen donor ligands [6]. In the case of bidentate ligands, there are at least two possible reaction outcomes, namely i) the formation of a six-coordinate copper complex by the addition of the bidentate ligand or ii) the replacement of the acetylacetonato ligand(s) resulting in the formation of a new copper complex [6], [7]. The reactions of Cu(acac)2, and derivatives, with bidentate N,N ligands have been the most frequently investigated, with very few examples of analogous reactions with potentially N,O bidentate ligands found in the literature. A relevant example of the latter is the bis(hexafluoroacetylacetonato) copper(II) complex with N-,O-chelating ethanolamine, which was prepared to evaluate its suitability as a synthetic precursor for copper thin films in the absence of an external reductant [8]. Herein, we report the synthesis and X-ray structure determination of the parent Cu(acac)2 complex with ethanolamine, (I).

The molecular structure of (I) is shown in the figure (70% displacement ellipsoids). The copper(II) atom is bis-chelated by two acac anions and a N-,O-chelating ethanolamine molecule. The Cu—O(acac) bond lengths formed by the O1-acac ligand are not equivalent, indicating an asymmetric mode of coordination, i.e. Cu—O1, O2 = 2.0070(15) and 2.0340(15) Å. These differences are also reflected in the associated C—O bond lengths with the shorter C1—O1 bond [1.256(3) Å] involving the more tightly bound O1 atom and the longer C3—O2 bond [1.278(3) Å] involving the less tightly bound O3 atom. This disparity in the Cu—O1, O2 bond lengths can be traced, in part, to the weak trans influence exerted by the weakly bound hydroxy-O5 donor atom of the neutral ethanolamine ligand; the O2 atom also participates in a hydrogen bonding interaction in the crystal (see below). For the O3-acac ligand the Cu—O3, O4 bond lengths are 2.0207(15) and 2.0216(15) Å, respectively, indicating a symmetric mode of coordination. For the ethanolamine ligand, the hydroxy-O5 atom forms the longest Cu—O distance in (I), i.e. 2.0992(15) Å; the Cu—N bond length is 2.1710(18) Å. The N2O4 donor set defines a distorted octahedral geometry with the three O1—Cu—O5, O2—Cu—O3 and O4—Cu—N1 trans angles being 174.91(6), 178.13(6) and 169.98(6)°, respectively. The mode of coordination of the acac ligands leads to the formation of six-membered chelate rings, neither of which is strictly planar. The best description of the configuration in each case in an envelope with the Cu atom being the flap atom, i.e. for the O1-chelate ring, the Cu atom lies 0.170(2) Å out of the plane through the remaining five atoms (O1, O2, C1—C3) which has a r.m.s. deviation = 0.0087 Å; the equivalent values for the O3-chelate are 0.238(2) and 0.0094 Å, respectively. The five-membered chelate ring defined by the chelating ethanolamine ligand, comprising the Cu, O5, N1, C11 and C12 atoms, has the most pronounced envelope configuration in (I) with the C12 atom lying 0.642(3) Å out of the plane through the remaining four atoms (r.m.s. deviation = 0.0102 Å).

The most prominent feature of the supramolecular association in the crystal is the formation of centrosymmetric dimeric aggregates sustained by hydroxy-O—H⋯O(acac) hydrogen bonding [O5—H5O⋯O2i: H5O⋯O2i = 1.862(16) Å, O5⋯O2i = 2.655(2) Å with angle at H5O = 163(3)° for symmetry operation (i) 1 − x, 1 − y, 2 − z]. These interactions involve the less tightly coordinating O2 atom (see above) and give rise to a non-planar eight-membered {⋯OHCuO}2 synthon. The dimeric aggregates are connected into a supramolecular chain approximately parallel to [1̄ 0 3] by methyl-C—H⋯O(acac) interactions [C4—H4c⋯O1ii: H4c⋯O1ii = 2.55 Å, C4⋯O1ii = 3.530(3) Å with angle at H4c = 174° for (ii) 2 − x, 1 − y, 1 − z]. The chains assemble in the crystal without directional interactions between them.

A further analysis of the supramolecular association was performed by calculating the Hirshfeld surfaces and two-dimensional fingerprint plots, i.e. both full and delineated plots, using established protocols [9] and Crystal Explorer [10]. The consideration of the supramolecular association described in detail above leads to supramolecular chains, surface contacts of the type O⋯H/H⋯O [14.3%] make a significant contribution. The most dominant surface contacts are H⋯H contacts, contributing in total 78.8% of all contacts in the crystal of (I) with the only other contribution to the surface contacts being from C⋯H/H⋯C contacts [6.9%].

Acknowledgements

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

References

1. Agilent Technologies: CrysAlisPRO. Agilent Technologies, Santa Clara, CA, U.S.A. (2010).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. Holtzclaw Jr, H. F.; Carlson, A. H.; Collman, J. P.: Polarographic reduction of copper chelates of 1,3-diketones. J. Am. Chem. Soc. 78 (1956) 1838–1840.10.1021/ja01590a018Search in Google Scholar

6. Bacchi, A.; Pelizzi, G.: Synthesis and structural characterization of copper(II) complexes with the 2′-[1-(2-pyridinyl)ethylidene]oxalohydrazide ligand. Trans. Metal Chem. 28 (2003) 935–938.10.1023/A:1026316611296Search in Google Scholar

7. Kurauchi, T.; Matsui, M.; Nakamura, Y.; Ooi, S.; Kawaguchi, S.; Kuroya, H.: Six-coordinate copper(II) complexes derived from the reactions of bis(acetylacetonato)- and bis(ethylacetoacetate)-copper(II) with some bidentate nitrogen bases. Bull. Chem. Soc. Japan 47 (1974) 3049–3056.10.1246/bcsj.47.3049Search in Google Scholar

8. Pinkas, J.; Huffman, J. C.; Bollinger, J. C.; Streib, W. E.; Baxter, D. V.; Chisholm, M. H.; Caulton, K. G.: Syntheses, structures, and thermal behavior of Cu(hfacac) complexes derived from ethanolamines. Inorg. Chem. 36 (1997) 2930–2937.10.1021/ic960370hSearch in Google Scholar PubMed

9. 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

10. 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

Received: 2019-08-11
Accepted: 2019-09-16
Published Online: 2019-10-11
Published in Print: 2019-12-18

©2019 Kong Mun Lo 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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  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-2019-0577
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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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