Home Crystal structure of 8-hydroxy-2-methylquinolin-1-ium chloride dihydrate, C10H14ClNO3
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Crystal structure of 8-hydroxy-2-methylquinolin-1-ium chloride dihydrate, C10H14ClNO3

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

C10H14ClNO3, monoclinic, P21/c (no. 14), a = 7.2706(2) Å, b = 14.8440(5) Å, c = 10.3910(3) Å, β = 101.101(2)°, V = 1100.46(6) Å3, Z = 4, Rgt(F) = 0.0268, wRref(F2) = 0.0735, T = 100(2) K.

CCDC no.: 1946612

The components of the asymmetric unit are 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 block
Size:0.09 × 0.08 × 0.05 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:2.99 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:67.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:13457, 1970, 0.034
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1815
N(param)refined:155
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.76794(4)0.62873(2)0.96240(3)0.01854(12)
O10.46747(13)0.62090(6)0.71185(9)0.0177(2)
H1O0.5471(19)0.6150(11)0.7807(12)0.027*
N10.25489(14)0.62173(7)0.47005(10)0.0129(2)
H1N0.3100(19)0.6710(8)0.5046(14)0.015*
C10.14860(17)0.62794(8)0.35021(12)0.0142(3)
C20.07143(17)0.54896(9)0.28740(12)0.0161(3)
H2−0.00610.55250.20280.019*
C30.10693(16)0.46717(9)0.34693(12)0.0154(3)
H30.05590.41420.30250.018*
C40.21923(16)0.46033(8)0.47446(11)0.0143(3)
C50.25945(17)0.37800(9)0.54184(12)0.0165(3)
H50.21290.32300.50150.020*
C60.36630(17)0.37799(9)0.66600(12)0.0173(3)
H60.39250.32260.71150.021*
C70.43780(17)0.45876(9)0.72709(12)0.0165(3)
H70.51040.45710.81350.020*
C80.40398(16)0.53999(9)0.66349(11)0.0141(3)
C90.29232(16)0.54120(8)0.53515(11)0.0132(3)
C100.11424(18)0.71830(9)0.28760(12)0.0191(3)
H10A0.04770.75640.34060.029*
H10B0.03810.71160.19940.029*
H10C0.23430.74630.28160.029*
O1W0.40536(13)0.78536(6)0.54775(9)0.0195(2)
H1W0.5107(15)0.7959(11)0.5272(16)0.029*
H2W0.3383(19)0.8292(9)0.5194(16)0.029*
O2W0.18351(13)0.92449(7)0.44925(10)0.0237(2)
H3W0.0733(16)0.9126(12)0.4609(17)0.035*
H4W0.206(2)0.9782(7)0.4747(17)0.035*

Source of material

All chemicals and solvents were used as purchased without further purification. The melting point was determined using a Mel-temp II digital melting point apparatus and was uncorrected. The solid-state IR spectrum was obtained on a Bruker Vertex 70v FTIR Spectrometer from 4000 to 400 cm−1.

Dibenzyltin dichloride was synthesized by the direct reaction of benzylchloride (Merck) and metallic tin powder (Merck) in toluene according to a literature procedure [5]. Dibenzyltin dichloride (0.37 g, 1 mmol) and 8-hydroxyquinaldine (Sigma Aldrich, 0.16 g, 1 mmol) were dissolved in methanol (20 mL) and the mixture was refluxed for 2 h. The filtrate was evaporated until a white precipitate was obtained. The precipitate was washed with n-hexane and recrystallized from a methanol solution. The title compound was isolated as a side-product obtained from the slow evaporation of the solvent. Yield: 0.05 g (21.6%). M.pt: 494–495 K. IR (cm−1): 1576 (m) ν(C—C), 1497 (s) ν(C—N), 1107 (s) ν(C—O).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The O- and N-bound H-atoms were located in a difference Fourier map but were refined with distance restraints of O—H = 0.84 ± 0.01 Å and N—H = 0.88 ± 0.01 Å, respectively, and with Uiso(H) set to 1.5Ueq(O) and 1.2Ueq(N), respectively.

Comment

The crystal structure of water-free 8-hydroxy-2-methylquinolinium chloride has been determined previously [6] as have its dihydrogen phosphate salt, isolated as a monohydrate [7], and 2-chloro-5-nitro-benzoate salt, as a dihydrate [8]. Further, there are examples of the monocation being the counterion to metal complex anions [9]. During the course of studies on the synthesis of dibenzyltin Schiff base compounds [10], see Source of Material, crystals of 8-hydroxy-2-methylquinolinium chloride became available as a dihydrate, (I).

The crystallographic asymmetric unit of (I) comprises an 8-hydroxy-2-methylquinolinium cation, a chloride anion and two water molecules as shown in the figure (70% displacement ellipsoids). As expected, the 10 atoms comprising the fused-ring system are co-planar, exhibiting a r.m.s. deviation of 0.013 Å. The planarity extends to the hydroxyl-O1 and methyl-C10 atoms, which lie 0.008(1) Å above and below the plane, respectively.

Significant hydrogen bonding is found in the crystal of (I). As indicated in the figure, there are charge-assisted hydroxy-O—H⋯Cl [O1—H1o⋯Cl1: H1o⋯Cl1 = 2.240(13) Å, O1o⋯Cl1 = 3.0617(10) Å with angle at H1o = 168.6(15)°] and pyridinium-N—H⋯O(water) [N1—H1n⋯O1w: H1n⋯O1w = 1.856(12) Å, N1⋯O1w = 2.7218(14) Å with angle at H1n = 169.1(13)°] hydrogen bonds as well as a water-O—H⋯O(water) [O1w—H2w⋯O2w: O1w—H2w⋯O2w = 1.866(14) Å, O1w—H2w⋯O2w = 2.6979(14) Å with angle at H2w = 177.5(17)°] hydrogen bonds providing direct links between the components of the asymmetric unit. The remaining water-O—H atoms form charge-assisted hydrogen bonds to the Cl1 atom [O1w—H1w⋯Cl1i: H1w⋯Cl1i = 2.385(13) Å, O1w⋯Cl1i = 3.2035(10) Å with angle at H1w = 162.3(15)°, O2w—H3w⋯Cl1ii: H3w⋯Cl1ii = 2.306(13) Å, O2w⋯Cl1ii = 3.1513(10) Å with angle at H3w = 171.7(17)° and O2w—H4w⋯Cl1iii: H4w⋯Cl1iii = 2.326(11) Å, O2w⋯Cl1iii = 3.1677(11) Å with angle at H4w = 173.6(14)° for symmetry operations (i) x, 3/2 − y, −1/2 + z, (ii) −1 + x, 3/2 − y, −1/2 + z and (iii) 1 − x, 1/2 + y, 3/2 − z]. This pattern of hydrogen bonding gives rise to a three-dimensional framework. Globally, the cations stack in columns parallel to the a axis with alternating pyridinium and C6 rings being almost superimposable, enabling the formation of π⋯π stacking interactions [Cg(N1,C1—C4,C9)⋯Cg(C4—C9)iv = 3.7016(7) Å with angle of inclination = 1.08(6)° for (iv) 1 − x, 1 − y, 1 − z] to further consolidate the packing.

A further analysis of the packing was made by calculating the Hirshfeld surfaces (including the full and delineated two-dimensional fingerprint plots) using Crystal Explorer 17 [11] and literature procedures [12]. The major contribution to the contacts of the overall asymmetric unit is from H⋯H, accounting for nearly half of all contacts, at 48.9%. Significant contacts also include Cl⋯H/H⋯Cl [18.9%], O⋯H/H⋯O [9.8%] C⋯H/H⋯C [9.0%] and C⋯C [8.6%], accounting for the bulk of the remaining contacts. An analysis was also performed for the individual water molecules as such calculations are useful in distinguishing between comparable molecules in a crystallographic asymmetric unit [13]. Indeed, significant differences are apparent in the percentage contributions to the individual surfaces of the water molecules reflecting the different hydrogen bonds formed by them. Thus, the major contributions to the Hirshfeld surface for the O1w-water molecule are H⋯H [50.3%], O⋯H/H⋯O [39.0%] and Cl⋯H/H⋯Cl [8.3%]. This compares with H⋯H [54.9%], O⋯H/H⋯O [28.4%] and Cl⋯H/H⋯Cl [14.0%] for the O2w-molecule. A comparison of the contacts formed by the two molecules shows decreased and increased contributions from O⋯H/H⋯O and Cl⋯H/H⋯Cl contacts, respectively, reflecting the formation of half the number of O—H⋯Cl hydrogen bonds for the O1w-water molecule compared with the O2w-water molecule.

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: 2019-07-28
Accepted: 2019-08-12
Published Online: 2019-09-11
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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  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-2019-0540
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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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