Home Physical Sciences Crystal structure of 12-(2-hydroxybenzoyl)benzo[f]pyrido[1,2-a]indole-6,11-dione, C23H13NO4
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Crystal structure of 12-(2-hydroxybenzoyl)benzo[f]pyrido[1,2-a]indole-6,11-dione, C23H13NO4

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Published/Copyright: September 27, 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

C23H13NO4, monoclinic, P21/n (no. 14), a = 11.6537(6) Å, b = 5.1315(2) Å, c = 26.8047(13) Å, β = 96.266(3)°, V = 1593.4(13) Å3, Z = 4, Rgt(F) = 0.0531, wRref(F2) = 0.1432, T = 90.0(5) K.

CCDC no.: 1941465

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:Orange lath
Size:0.31 × 0.17 × 0.03 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.11 mm−1
Diffractometer, scan mode:Bruker Kappa APEX-II, φ and ω
θmax, completeness:30.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:14398, 4810, 0.049
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3317
N(param)refined:256
Programs:Bruker [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.56928(11)−0.2702(2)0.06371(5)0.0191(3)
O20.39483(10)0.5568(2)0.15726(5)0.0177(3)
O30.09611(11)0.5444(2)0.06004(4)0.0197(3)
O4−0.00752(11)0.7681(2)0.12774(5)0.0218(3)
H4O0.010(2)0.717(4)0.0973(10)0.033*
N10.33258(12)−0.0672(2)0.03466(5)0.0134(3)
C10.52921(14)−0.0858(3)0.08571(6)0.0138(3)
C20.41347(14)0.0127(3)0.07365(6)0.0135(3)
C30.36254(14)0.2088(3)0.09978(6)0.0139(3)
C40.43211(14)0.3608(3)0.13882(6)0.0133(3)
C50.55334(14)0.2688(3)0.15213(6)0.0132(3)
C60.62359(14)0.4053(3)0.18879(6)0.0154(3)
H60.59260.54580.20610.018*
C70.73880(15)0.3358(3)0.19995(6)0.0171(3)
H70.78650.42980.22480.021*
C80.78447(15)0.1301(3)0.17505(6)0.0174(3)
H80.86370.08560.18230.021*
C90.71445(15)−0.0109(3)0.13952(6)0.0161(3)
H90.7455−0.15540.12340.019*
C100.59931(14)0.0572(3)0.12727(6)0.0136(3)
C110.34066(15)−0.2625(3)−0.00030(6)0.0153(3)
H110.4077−0.36870.00090.018*
C120.25092(15)−0.2995(3)−0.03641(6)0.0166(3)
H120.2547−0.4353−0.06030.020*
C130.15200(15)−0.1385(3)−0.03890(6)0.0171(3)
H130.0912−0.1625−0.06510.021*
C140.14328(14)0.0519(3)−0.00369(6)0.0153(3)
H140.07690.1602−0.00540.018*
C150.23385(14)0.0853(3)0.03506(6)0.0138(3)
C160.24945(14)0.2513(3)0.07717(6)0.0138(3)
C170.15555(14)0.4160(3)0.09268(6)0.0133(3)
C180.12771(13)0.4131(3)0.14494(6)0.0127(3)
C190.04765(14)0.5944(3)0.16008(6)0.0141(3)
C200.02286(14)0.6000(3)0.21010(6)0.0165(3)
H20−0.02740.72940.22080.020*
C210.07135(14)0.4179(3)0.24362(6)0.0159(3)
H210.05360.42150.27740.019*
C220.14633(14)0.2279(3)0.22882(6)0.0156(3)
H220.17780.10010.25210.019*
C230.17427(14)0.2274(3)0.18005(6)0.0141(3)
H230.22590.09910.17000.017*

Source of material

To a solution of 2,3-dichloronaphthalene-1,4-dione (0.5 g, 2.2 mmol) in anhydrous pyridine (50 mL), (E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one (0.49 g, 2.2 mmol) was added and heated to 85 °C. After 24 h, the mixture was cooled to room temperature and diluted with water (250 mL) and the resulting precipitate was collected via filtration, dried and purified by preparative TLC (silica gel thickness = 1000 microns, 20 cm × 20 cm) using chloroform and methanol as mobile phase (20:1 v/v) to yield an orange solid. The solid was crystalized with a few drops of methanol in chloroform to furnish orange colored crystals. The melting point was determined as 537–538 K using a XT-4 melting point instrument (Beijing Taike Instrument Co., Ltd, China). NMR spectra were performed on a DRX-500 Bruker NMR spectrometer (Bruker, Germany). 1H-NMR (500 MHz, CDCl3) δ: [ppm] 12.22 (1H, s), 9.82 (1H, d, J = 7.0 Hz), 8.30 (1H, d, J = 7.5 Hz), 8.13 (1H, d, J = 7.6 Hz), 7.79∼7.76 (2H, m), 7.70 (1H, t, J = 7.5 Hz), 7.55∼7.50 (2H, m), 7.39 (1H, t, J = 7.5 Hz), 7.21 (1H, t, J = 6.7 Hz), 7.13 (1H, d, J = 8.3 Hz), 6.79 (1H, t, J = 7.6 Hz); 13C-NMR (125 MHz, CDCl3) δ: [ppm] 196.3, 180.9, 174.9, 162.8, 138.1, 136.7, 134.4, 133.9, 133.5, 133.2, 133.2, 128.2, 128.0, 127.4, 127.2, 126.4, 121.4, 120.8, 119.9, 118.8, 118.4, 117.6, 112.5. IR (νmax, cm−1): 2953, 2920, 2851; 1662, 1638, 1619; 1578, 1496, 1466, 1430; 1388, 1366, 1312, 1289, 1254, 1220, 1189, 1146, 1108, 1062, 877, 844, 747. ESI-MS: 368.0 [M + 1]+; ACPI-MS: 368.0 [M + 1]+, 366.8 [M − 1]−.

Experimental details

H atoms were positioned geometrically with d (O—H) = 0.90 Å, d(C—H) = 0.95 Å (aromatic CH), and treated as riding atoms. For all H atoms, isotropic displacement parameters were calculated as Uiso(H) = 1.2 Ueq(C) and Uiso(H) = 1.5Ueq(O).

Comment

The naphthofuranoquinone core which is integral part of various anticancer natural products such as Balsaminone A [4] was achieved via simple base-catalyzed condensation reaction between 1,4-naphthoquinone and the corresponding phenol. Intermolecular O-alkylation followed by intramolecular C—C-bond formation are believed to be essential steps for the formation of naphthofuranoquinone scaffold [5]. In an attempt to synthesize the naphthofuranoquinones derived from coupling of 1,4-naphthoquinone with trans-2′-hydroxychalcone resulted an unusual compound instead of naphthofuranoquinone. Crystal structure analysis confirmed the formation of benzpyrido[1,2-a]indoledione as the product. This intermolecular cyclization mechanism was very interesting and formation of such product with 2′-hydroxy acetophenone is reported. In order to form such fused compounds, it appears that the building block o-hydroxy acetophenone was generated in situ from trans-2′-hydroxychalcone via some kind of retro-aldol-like decomposition [6]. A different method of synthesizing the compound directly using substituted acetophenone react with 1,4-naphthoquinone confirmed this mechanism [7]. The title crystal structure is only built up by C23H13NO4 molecules, in which all geometric parameters are normal. There is an intramolecular hydrogen bond: O4—H4O⋯O3 (d(O4—H4O⋯O3) = 2.559 Å; α(O4—H4O⋯O3) = 151°. During a database search for the molecular core scaffold, three crystal structures were found viz. 12-Benzoyl-2-methylbenzo[1,2-a]indole-6,11-dione [8]; 12-(4-Chlorobenzoyl)-2-methylbenzo[f] pyrido[1,2-a]indole-6,11-dione [7] and 12-(4-Methoxybenzoyl)-2-methyl-benzo[f]pyrido[1,2-a] indole-6,11-dione [9]. With a hydroxy group instead of methyl, methyl/chloro or methyl/methoxy group, the title crystal shows a different hydrogen bonding scheme.

Acknowledgements

This work was supported by grants from State Scholarship Fund awarded by China Scholarship Council (grant no. 201706660015), Guangxi Scholarship Fund of Guangxi Education Department (grant no. guijiaoshipei 2016-22), Promotion of Young and Middle-aged Teachers’ Basic Scientific Research Ability in Guangxi Universities by Guangxi Education Department (grant no. 2019KY0329), GuangXi Key Laboratory of Zhuang and Yao Ethnic Medicine and Guangxi Colleges and Universities Key Laboratory of Chinese Medicine Extraction Purification and Quality Analysis (grant no. J16067-11).

References

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Received: 2019-07-23
Accepted: 2019-09-16
Published Online: 2019-09-27
Published in Print: 2019-12-18

©2019 Peng Luo 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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  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-2019-0524
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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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