Startseite Crystal structure of bis{(N-[(5-chloro-2-oxidophenyl)methylidene]-2-hydroxybenzenecarbohydrazonato)-dioxo-molybdenum(VI)}(μ2-4,4′-bipyridine), C38H26Cl2Mo2N6O10
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Crystal structure of bis{(N-[(5-chloro-2-oxidophenyl)methylidene]-2-hydroxybenzenecarbohydrazonato)-dioxo-molybdenum(VI)}(μ2-4,4′-bipyridine), C38H26Cl2Mo2N6O10

  • Kong Mun Lo , See Mun Lee und Edward R.T. Tiekink ORCID logo EMAIL logo
Veröffentlicht/Copyright: 11. Oktober 2019
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 235 Heft 1

Abstract

C38H26Cl2Mo2N6O10, triclinic, P1̄ (no. 2), a = 7.7151(2) Å, b = 10.5336(2) Å, c = 12.5668(2) Å, α = 73.027(2)°, β = 76.226(2)°, γ = 72.269(2)°, V = 917.83(4) Å3, Z = 1, Rgt(F) = 0.0234, wRref(F2) = 0.0612, T = 100(2) K.

CCDC no.: 1953496

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:Brown prism
Size:0.12 × 0.08 × 0.07 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:7.54 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:67.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:21955, 3275, 0.030
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3250
N(param)refined:263
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Mo0.55579(2)0.32783(2)0.31241(2)0.01358(8)
Cl1−0.09949(8)0.14896(6)0.83536(5)0.02601(14)
O10.6590(2)0.25368(16)0.20158(14)0.0185(3)
O20.7201(2)0.28583(18)0.39486(14)0.0218(4)
O30.3947(2)0.21441(16)0.40121(13)0.0174(3)
O40.5864(2)0.51599(16)0.23371(13)0.0168(3)
O50.3506(2)0.86723(18)0.37065(15)0.0238(4)
H5O0.33180.78880.39850.036*
N10.3595(3)0.47508(19)0.41200(16)0.0138(4)
N20.3761(3)0.6092(2)0.37409(16)0.0160(4)
N30.2983(3)0.4181(2)0.20163(16)0.0165(4)
C10.2799(3)0.2048(3)0.50102(19)0.0175(5)
C20.2291(3)0.0809(2)0.5502(2)0.0204(5)
H20.27500.00770.51300.024*
C30.1131(3)0.0648(3)0.6520(2)0.0223(5)
H30.0799−0.01950.68580.027*
C40.0444(3)0.1733(3)0.7055(2)0.0208(5)
C50.0874(3)0.2970(3)0.6575(2)0.0201(5)
H50.03690.37010.69460.024*
C60.2070(3)0.3156(2)0.5530(2)0.0174(5)
C70.2454(3)0.4479(2)0.50422(19)0.0167(5)
H70.18330.51950.54190.020*
C80.4978(3)0.6212(2)0.2808(2)0.0169(5)
C90.5398(3)0.7530(2)0.2240(2)0.0171(5)
C100.4658(3)0.8681(3)0.2709(2)0.0190(5)
C110.5138(4)0.9908(3)0.2135(2)0.0224(5)
H110.46611.06850.24540.027*
C120.6297(4)1.0003(3)0.1111(2)0.0238(5)
H120.66121.08450.07310.029*
C130.7013(4)0.8882(3)0.0626(2)0.0233(5)
H130.77980.8959−0.00860.028*
C140.6568(3)0.7651(3)0.1192(2)0.0190(5)
H140.70590.68800.08660.023*
C150.3036(4)0.5211(3)0.1091(2)0.0214(5)
H150.39160.57240.09730.026*
C160.1891(4)0.5573(3)0.0300(2)0.0227(5)
H160.19840.6325−0.03310.027*
C170.0604(3)0.4839(2)0.04265(19)0.0164(5)
C180.0524(3)0.3773(3)0.1394(2)0.0240(5)
H18−0.03420.32440.15310.029*
C190.1703(3)0.3488(3)0.2151(2)0.0230(5)
H190.16100.27630.28040.028*

Source of material

All chemicals and solvents were used as purchased without further purification. The melting point was determined on a Mel-temp II digital melting point apparatus and was uncorrected. The IR spectrum was obtained on a Bruker Vertex 70v FTIR Spectrometer in the range 4000 to 400 cm−1. The 1H NMR spectrum was recorded in DMSO-d6 solution on a Bruker Ascend 400 MHz NMR spectrometer with chemical shifts relative to tetramethylsilane.

The Schiff base molecule was synthesized from the reaction of 5-chlorosalicylaldehyde (Sigma-Aldrich) and 2-hydroxybenzhydrazide (Fluka) in a 1:1 molar ratio. Bis(acetylacetonato)dioxomolybdenum(VI) (Sigma Aldrich, 0.33 g, 1 mmol) and the Schiff base (0.29 g, 1 mmol) were dissolved in methanol (30 mL) and the mixture was refluxed for 2 h. Next, 4,4′-bipyridine (Sigma Aldrich, 0.08 g, 0.5 mmol) was added into the mixture. After filtration, the filtrate was evaporated slowly until light-brown crystals were formed. The crystals were filtered, washed with a minimum amount of methanol and air-dried in vacuo over P4O10. Yield: 0.24 g (49%). M.pt: 491–493 K. IR (cm−1) 1610 (m) ν(C—N), 1601 (s) ν(C—N), 1542 (s) ν(C—O), 1343 ν(C—O), 1261 ν(C—O), 1092 (m) ν(C—O), 931(m) ν(Mo—O), 902 (m) ν(Mo—O). 1H NMR (DMSO-d6, ppm): δ 6.98–7.04 (m, 6H, Ph—H), 7.87 (d, 4H, J = 9.10 Hz, py—H), 7.59 (d, 4H, J = 8.81 Hz, py = H), 7.60–7.83 (m, 8H, Ph—H), 8.73 (s, 2H, NCH), 11.33 (s, 2H, OH).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The O-bound H-atom was also geometrically placed (O—H = 0.84 Å) and refined as riding with Uiso(H) = 1.5Ueq(O). The maximum and minimum residual electron density peaks of 1.14 and 0.55 eÅ−3, respectively, were located 0.63 and 0.72 Å from the H11 and Mo atom, respectively, i.e. in chemically non-sensible positions.

Comment

Di-basic, tridentate Schiff base ligands containing two terminal hydroxy/phenol sites are known to form complexes with many metal ions. Without exception, the reaction of dioxomolybdenum cations with these Schiff base ligands results in the formation of six-coordinate complexes with the sixth coordination site occupied by a solvent molecule, as found in the structure related to the title structure [5], or, through dimerisation, via bridging through a donor atom of the complexing ligand. The presence of a labile site in these mononuclear dioxomolybdenum(VI) complexes also allows the binding and displacement of different substrate molecules [6], [7]. Further, these complexes have attracted research interest over the decades for their possible anti-tumour [8], anti-fungal [9] and anti-viral [10] properties. In this work and in continuation of structural studies in this area [11], the synthesis and X-ray crystal structure of the title binuclear molybdenum(VI) complex, MoO2(L)(4,4′-bipyridine)MoO2(L), (I), where H2L is 4-chloro-2-[(1E)-[(Z)-2-[2-hydroxy-2-(2-hydroxyphenyl) ethylidene]hydrazin-1-ylidene]methyl]phenol, are described.

The binuclear molecule in (I) is disposed about a crystallographic centre of inversion and is shown in the figure (70% probability displacement ellipsoids; unlabelled atoms are related by the symmetry operation (i) −x, 1 − y, −z). The Mo(VI) centre is complexed by the oxo-O1 and O2 atoms, the phenoxide-O3, oxide-O4 and imine-N1 atoms, derived from the tridentate Schiff base di-anion, and the pyridyl-N3 atom of the μ2-bridging 4,4′-bipyridine molecule. The resulting N2O4 donor set describes an octahedral geometry where the oxo groups are cis, and where the three donor atoms of L2− anion occupy mer positions. An intramolecular hydroxy-O—H⋯N(imine) hydrogen bond [O5—H5o⋯N2: H5o⋯N2 = 1.92 Å, O5⋯N2 = 2.653(3) Å with angle at H5o = 145°] closes an S(6) loop. The tridentate mode of coordination of the Schiff base di-anion results in the formation of five- and six-membered chelate rings. The acute angles subtended by these rings [O3—Mo—N1 = 80.87(7)° and O4—Mo—N1 = 72.13(6)°] are primarily responsible for the deviation of the O3—Mo—O4 angle [148.10(7)°] from linearity. To a first approximation, the five-membered ring is planar with the r.m.s. deviation of the fitted atoms being 0.0355 Å with maximum deviations above and below the best plane being 0.0361(7) and 0.0448(11) Å for the Mo and O4 atoms, respectively. An alternate description of the five-membered chelate ring would be one based on an envelope configuration where the Mo flap atom lies 0.174(4) Å out of the plane defined by the four remaining atoms (r.m.s. deviation = 0.0013 Å). Such a description is certainly apt for the six-membered ring whereby the Mo atom lies 0.426(3) Å out of the least-squares plane defined by the five remaining atoms of the chelate ring (r.m.s. deviation = 0.0171 Å). The dihedral angle formed between the best plane through each chelate ring is 6.15(13)°. The dihedral angles between the five-membered chelate ring and pendent hydroxyphenyl ring is 8.23(11)°, between the six-membered chelate ring and fused chlorophenyl ring is 6.92(10)° and between the peripheral rings is 2.90(12)°, all suggesting that to a first approximation, the Schiff base di-anion is planar. The attached pyridyl ring is inclined with respect to the five- and six-membered rings as seen in the respective dihedral angles of 67.03(6) and 63.06(6)°.

In the molecular packing of (I), weak hydroxy-O—H⋯O(oxide) [O5—H5O⋯O2ii: H5O⋯O2ii = 2.45 Å, O5⋯O2ii = 2.929(2) Å with angle at H5O = 117° for (ii) 1 − x, 1 − y, 1 − z], chlorophenyl-C—H⋯O(hydroxy), [C2—H2⋯O5iii: H2⋯O5iii = 2.50 Å, C2⋯O5iii = 3.422(3) Å with angle at H2 = 163° for (iii) x, −1 + y, z], pyridyl-C—H⋯O(oxide) [C16—H16⋯O1iv: H16⋯O1iv = 2.31 Å, C16⋯O1iv = 3.197(3) Å with angle at H16 = 155° and C18—H18⋯O1v: H18⋯O1v = 2.58 Å, C18⋯O1v = 3.493(3) Å with angle at H18 = 162° for (iv) 1 − x, 1 − y, −z and (v) −1 + x, y, z] along with π⋯π stacking between chlorophenyl and hydroxyphenyl rings [inter-centroid Cg(C1—C6)⋯Cg(C9—C14)ii distance = 3.6605(15) Å with angle of inclination = 2.90(13)°] sustain a three-dimensional architecture.

An additional analysis was conducted to probe the molecular packing further. Thus, Crystal Explorer 17 [12] was employed to calculate the percentage contributions to the Hirshfeld surfaces as well as the full and delineated fingerprint plots for the entire binuclear molecule, following literature protocols [13]. This analysis showed the importance of several different contacts to the surface but, with the most prominent due to just two types of contact, namely H⋯H [51.6%] and O⋯H/H⋯O [30.6%] contacts, accounting for over 80% of all surface contacts. Significant contributions are also made by C⋯H/H⋯C [6.6%], C⋯C [6.2%], O⋯O [3.6%] and O⋯C C⋯O [1.5%] contacts.

Acknowledgements

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

References

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Received: 2019-08-05
Accepted: 2019-09-13
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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  5. Crystal structure of 1,1′-methylenebis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C11H18F12N4P2
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  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
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  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
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  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
https://doi.org/10.1515/ncrs-2019-0566
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Artikel in diesem Heft

  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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