Home Physical Sciences Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C19H18O8
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Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C19H18O8

  • Iván Brito EMAIL logo , Jorge Bórquez , Mario Simirgiotis and Alejandro Cárdenas
Published/Copyright: November 16, 2017
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 233 Issue 1

Abstract

C19H18O8, monoclinic, P21/c (no. 14), a = 12.689(2) Å, b = 20.321(4) Å, c = 7.0820(13) Å, β = 105.368(13)°, V = 1760.8(6) Å3, Z = 4, Rgt = 0.0662, wRref(F2) = 0.1788, T = 295 K.

CCDC no.:: 1581467

The title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow block
Size:0.22 × 0.20 × 0.10 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:0.94 mm−1
Diffractometer, scan mode:Bruker D8-Venture, φ and ω-scans
θmax, completeness:59.6°, >98%
N(hkl)measured, N(hkl)unique, Rint:27492, 2531, 0.317
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1251
N(param)refined:251
Programs:Bruker programs [27], SHELX [28], OLEX2 [29]
Table 2:

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

AtomxyzUiso*/Ueq
O10.6930(2)0.39194(13)0.6743(4)0.0469(9)
O20.4768(2)0.39502(15)0.6405(5)0.0586(10)
O30.3695(2)0.28331(15)0.6637(5)0.0666(11)
O40.6911(2)0.15607(13)0.7049(5)0.0654(10)
H40.75690.16180.72300.098*
O50.8656(2)0.22207(14)0.6981(5)0.0586(10)
O60.9641(2)0.34225(13)0.6641(4)0.0538(9)
O71.0806(2)0.56956(13)0.7812(5)0.0570(10)
O80.9222(2)0.66056(13)0.6624(5)0.0620(10)
H80.98880.66460.70010.093*
C1′0.8346(3)0.46317(19)0.6687(7)0.0406(12)
C2′0.9446(3)0.4822(2)0.7249(7)0.0453(13)
H2′0.99830.45020.76370.054*
C3′0.9753(3)0.5473(2)0.7243(6)0.0423(12)
C4′0.8951(4)0.5955(2)0.6645(7)0.0458(12)
C5′0.7876(3)0.5781(2)0.6054(7)0.0486(13)
H5′0.73470.61030.56190.058*
C6′0.7563(3)0.5127(2)0.6097(7)0.0479(13)
H6′0.68250.50180.57290.057*
C20.8006(3)0.3949(2)0.6779(6)0.0389(12)
C30.8600(3)0.3391(2)0.6846(6)0.0424(12)
C40.8125(3)0.2743(2)0.6939(6)0.0446(12)
C50.6404(4)0.2148(2)0.6947(7)0.0473(13)
C60.5310(4)0.2166(2)0.6854(7)0.0538(14)
H60.49260.17760.68590.065*
C70.4774(3)0.2771(2)0.6750(7)0.0489(13)
C80.5325(3)0.3358(2)0.6675(7)0.0464(12)
C90.6415(3)0.3330(2)0.6786(6)0.0399(12)
C100.6998(3)0.2739(2)0.6918(6)0.0419(12)
C160.4761(5)0.4283(3)0.8144(10)0.109(2)
H16A0.44800.47200.78360.163*
H16B0.54920.43070.89770.163*
H16C0.43060.40490.88050.163*
C170.3041(4)0.2245(2)0.6496(8)0.0830(19)
H17C0.30980.19920.53830.125*
H17A0.22910.23650.63470.125*
H17B0.32980.19880.76640.125*
C181.0481(4)0.3224(2)0.8311(8)0.0777(19)
H18A1.11810.33260.81090.117*
H18B1.04300.27590.85050.117*
H18C1.03960.34540.94460.117*
C191.1645(3)0.5215(2)0.8348(7)0.0569(14)
H19A1.16040.49230.72650.085*
H19B1.15540.49680.94500.085*
H19C1.23450.54290.86910.085*

Source of material

The title compound is a highly biologically active poly-methoxylated flavonoid, which is anti-inflammatory and antiproliferative [1, 2] , can inhibit leukocyte chemotaxis and oxygen free radical formation [3, 4] and prevents cyclophosphamide and ifosfamide-induced hemorrhagic cystitis in rats [5]. The title compound was isolated using medium pressure column chromatography (MPCC) from Parastrephia quadrangularis, a medicinal plant used by the Aymara Amerindians [6, 7] , a known producer of several flavonoids and benzoic acid derivatives with antioxidant activity [8], [9], [10], [11]. Following our program to isolate interesting metabolites from the Atacama Desert Flora, Northern Chile [12], [13], [14], [15], [16], [17], [18], dried aerial parts of P. quadrangularis (1622 g) collected in april 2015 in “El Tatio”, Andean mountain range of the of Atacama Desert, II Region, Northern Chile, were defatted with hexane (3 liters, 3 times in the dark, 24 hours each time) and 54.82 g were obtained after evaporation of the solvent. Then the plant material was extracted with ethyl acetate (3 liters, 3 times in the dark, 24 hours each time. After evaporation of the solvent under vacuo at 40 oC, 485 g of a dark gummy extract was obtained. A portion of the extract (10.0 g) was filtered and submitted to a medium pressure column chromatography system composed of an 2.5 cm × 48 cm medium pressure column packed with silicagel using an isocratic solvent system of n-hexane-ethyl acetate (8.0:2.0 v:v) pumped with a medium pressure pump with a flow rate of 10 mL-minute. The collected fractions (120) were combined according to TLC analysis (Kieselgel F254 plates, developed with hexane: EtOAc 7:3 v/v, and spots visualized by spraying with vanillin: sulfuric acid 2% in ethanol and heating) and twenty combined fractions were obtained. Fraction 15, enriched in flavonoids (120 mg) was re-chromatographed using Sephadex LH 20 (200 g, solvent methanol) and 60 fractions (S1–S60) were obtained. From fractions S25–33, the known compound: 5,7,4′-trihydroxy-3,8,3′trymethoxyflavone (25 mg) was isolated and from fractions S45–57 the title compound (15 mg) was isolated. The NMR data for both compounds are consistent with literature [19], [20], [21], [22], [23]. Recrystallization from ethyl acetate at room temperature yielded pure yellow crystals of the title compound (8 mg). Yellow crystals, m.p. 215–217 °C. The molecular weight was determined by HESI-MS/MS with a mass spectrometer (Q-exactive Focus, Bremen, Germany) [M—H]−: 373.09290, calcd. for C19H17O8−: 373.09289. 1H NMR (Bruker Avance 300 MHz, CDCl3) δ ppm: 7.80 (1H, s, H-2′), 7.79 (1H, d, J = 9.0 Hz, H-6′), 7.07 (1H, d, J = 9.0 Hz, H-5′), 6.42 (1H, s, H-6), 6.09 (1H, s, 4′-OH), 12.5 (1H, s, 5-OH), 3.99 (3H, s, OCH3), 3.95 (3H, s, OCH3), 3.92 (3H, s, OCH3), 3.88 (3H, s, OCH3). 13C NMR (13C NMR Bruker Avance 75 MHz, DMSO-d6) δ ppm: 158.4 (C-2), 138.6 (C-3), 179.01 (C-4), 157.3 (C-5), 95.4 (C-6), 155.8 (C-7), 128.7 (C-8), 148.5 (C-9), 105.3 (C-10), 122.9 (C-1′), 110.8 (C-2′), 148.4 (C-3′), 146.4 (C-4′), 114.8 (C-5′), 122.6 (C-6′), 61.6 (O-CH3), 60.2 (O-CH3), 56.4 (O-CH3), 56.0 (O-CH3). These data, together with ESI-MS/MS and correlations observed in the HSQC and HMBC spectra, are consistent with the structure of the title compound (cf. the figure) confirmed by comparison of spectroscopic data with those reported in the literature for this structure [19, 20] and other similar methoxilated flavones [21], [22], [23].

Experimental details

H atoms were refined with fixed individual displacement parameters, using a riding model with C—H distances of 0.93 Å (for aromatic rings), 0.96 Å ( for CH3 group) and O—H of 0.86 Å with U(H) values of 1.2Ueq(C,O) (for CH in aromatic moiety and OH group), and 1.5Ueq(C) (for CH3). Problems during data collection and the successive reduction yielded many reflections with a negative intensity, which produced a non-optimal Rint factor. Nevertheless the topology of this structure is in any case correct.

Discussion

The title compound (1) is a positional isomer of 5-hydroxy-2-(3′-hydroxy-4-methoxyphenyl)-3,6,7′-trimethoxychromen-4-one (casticin) (2) [24] and 5,12-Dihydroxy-2,6,7,13-tetramethoxyflavone (3) [25]. In the compounds (2) and (3) the fused chromene ring system and the benzene ring bonded to it are close to coplanar, with a dihedral angle between their respective mean planes of: 8.30(12)° and 2.7(1)° for (2) and (3) respectively, however for the compound (1) the dihedral angle value is 17.17(18)°, which is the main difference with the isomers (2) and (3). The two hydroxy H atoms of the title compound are involved in intramolecular and intermolecular O—H⋯O hydrogen bonding in the solid state. Intramolecular O4—H4⋯O5 and intermolecular O8—H8⋯O5 (2 − x, 1/2 + y, 1/2 − z) hydrogen bonds and π-π interactions help to stabilize the crystal structure. In the crystal packing the molecules are associated by one strong intermolecular hydrogen bond forming zig-zag chain with graph-set motif C(10) [26] along [010] direction. All distances and angles are normal and comparable with the compounds (2) and (3).

Acknowledgements

IB thanks to Fondequip (EQM13-0021). JB and MS thanks to FONDECYT (Chile) (Grant 1140178) and DID-PEF 2017 Universidad Austral de Chile for financial support.

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Received: 2017-7-13
Accepted: 2017-10-23
Published Online: 2017-11-16
Published in Print: 2018-1-26

©2018 Iván Brito et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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  31. Crystal structure of Ga0.62(3)Sb0.38(3)Pd3
  32. Crystal structure of Ga0.47(1)Sb0.53(1)Pd2
  33. A derivative of the Corey lactone – crystal structure of (3aR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate, C21H30O5Si
  34. A Corey lactone: crystal structure of (3aR,4R,5R,6aS)-5-benzoyloxy-4(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one, C15H16O5
  35. Hydrothermal synthesis and crystal structure of poly[aqua-(μ2-1,3-bis(4-pyridyl)propane-κ2N:N′)-(μ2-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylato-κ2O:O′)manganese(II) hydrate, C22H20Cl6N2O6Mn
  36. Crystal structure of 2-acetylpyrrole S-methylthiosemicarbazonium hydroiodide, C8H13IN4S
  37. Crystal structure of [N,N-bis((pyrrol-2-yl)ethylidene)butane-1,4-diamine-κ4N,N′,N′′,N′′′]-nickel(II), C16H20N4Ni
  38. Crystal structure of poly[aqua-(μ5-2,5-dicarboxybenzoato-κ5O:O:O′:O′′:O′′′)sodium(I)], C9H7NaO7
  39. Crystal structure of bis(N′-((1H-pyrrol-2-yl)methylene)-1-methylthio-methanethiohydrazido-κ2S,N)nickel(II), C14H16N6NiS4
  40. Crystal structure of 1-(4-((benzo[d][1,3]dioxol-5-yloxy)methyl)phenethyl)-4-(3-chlorophenyl) piperazin-1-ium chloride, C26H28Cl2N2O3
  41. Crystal structure of 2-(4-(2-(4-(2-fluorophenyl)piperazin-1-yl)ethyl)benzyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide, C26H26FN3O3S – a saccharin dervative
  42. Crystal structure of 3-(2-dimethylaminoethyl)-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C12H15N3OS
  43. Crystal structure of 3-(3-dimethylaminopropyl)-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C13H17N3OS
  44. The crystal structure of trans-tetraaqua-bis(p-tolylsulfinato-κO)calcium(II)), C14H22O8S2Ca
  45. The crystal structure of (E)-N′-(pyridin-2-ylmethylene)pyrazine-2-carbohydrazide, C11H9N5O
  46. Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C24H15NO
  47. Crystal structure of catena-poly[diaqua-(μ2-tartrato-κ4O,O′:O′′,O′′′)cobalt(II)], C4H8CoO8
  48. Crystal structure of 4-chloro-2-methyl-6-(4-(trifluoromethoxy)phenyl)pyrimidine, C12H8ClF3N2O
  49. Crystal structure of 1-(4-fluorophenyl)-N-(5-((triphenylstannyl)thio)thiophen-2-yl)methanimine, C27H20FN3S2Sn
  50. Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C10H8FN3OS2
  51. Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C22H31N5O4S2
  52. The crystal structure of (E)-2-((2-(o-tolylcarbamothioyl)hydrazono)methyl)benzoic acid, C16H15N3O2S
  53. Crystal structure of 2-chloro-1,3-di-tert-pentyl-4,4-diphenyl-1,3,2λ3,4-diazaphosphasiletidine, C22H32ClN2PSi
  54. Crystal structure of tetramethyl 5,5′-(buta-1,3-diyne-1,4-diyl)diisophthalate, C24H18O8
  55. Crystal structural of 2-amino-4-(4-methoxyphenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran, C19H20N2O3
  56. Crystal structure of 1,3,5-tris((trimethylsilyl)methyl)-1,3,5-triazinane-2,4,6-trione, C15H33N3O3Si3
  57. The crystal structure of bis(2-benzoyl-5-hydroxylphenolato-κ2O,O′)copper(II), C26H18CuO6
  58. Crystal structure of 2,6-bis(3-(pyrazin-2-yl)-1H-1,2,4-triazol-5-yl)pyridine – 1-ethyl-3-methyl-1H-imidazol-3-ium bromide (1/1), C23H22N13Br
  59. The crystal structure of (E)-N-benzyl-N′-benzylidene-4-methylbenzenesulfonohydrazide, C21H20N2O2S
  60. Crystal structure of ethyl (E)-5-((2-(3-hydroxybenzoyl)hydrazono)methyl)-3,4-dimethyl-1H-pyrrole-2-carboxylate – water – ethanol (1/1/1), C19H27N3O6
  61. The crystal structure of (E)-4-(3-ethoxy-2-hydroxybenzylideneamino)benzoic acid, C16H15NO4
  62. Crystal structure of (μ2-N,N′-bis((pyridin-4-yl)methyl)ethanediamide-κ2N:N′)-tetrakis(diethylcarbamodithioato-κ2S,S′)dizinc(II), C34H54N8O2S8Zn2
https://doi.org/10.1515/ncrs-2017-0141
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Editorial 2018
  3. Crystal structure of dimethanol-bis{3-(((2-oxidonaphthalen-1-yl)methylene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N:O′}dizinc(II), C42H30Zn2N2O10
  4. Crystal structure of aqua-bis{[2,6-dimethyl-N-(pyridin-2-ylmethylene)aniline-κ2N,N′]}zinc(II) triflate monohydrate [ZnC29H31N4O]CF3SO3⋅H2O
  5. Crystal structure of (E)-1-(4-{[(E)-4-Diethylamino-2-hydroxybenzene methylene]amino}phenyl)ethanone methoxy oxime, C20H27ClN3O3
  6. Crystal structure of (E)-1-(4-(((E)-4-(diethylamino)-2-hydroxybenzylidene)amino)phenyl)ethan-1-one oxime, C19H23N3O2
  7. Crystal structure of poly[(μ2-1,4-bis((2-ethyl-1H-benzo[d]imidazol-1-yl)methyl)benzene-κ2N:N′)-(μ2-4,4′-sulfonyldibenzoato-κ2O:O′)zinc(II)], C40H34N4O6SZn
  8. Crystal structure of catena-poly[diaqua(μ3-pyrazine-2,3-dicarboxylato-κ4O,N:O′:O′′)zinc(II)] 1.25 hydrate, C6H8.5N2O7.25Zn
  9. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(tri-m-tolyl phosphane-κP)rhenium(I), C29H28O5PRe
  10. Crystal structure of bis(μ2-methanolato-κ2O:O)-bis(methanol-κ1O)-bis{3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ3O,O′,N}dichromium(III), C38H36Cr2N2O14
  11. Crystal structure of poly[aqua-(μ3-pyridine-3,5-dicarboxylato-κ5O,O′:O′′,O′′′,N)zinc(II)], C7H7NO6Zn
  12. Crystal structure of bis((1-(((4-(((benzyloxy)imino)methyl)phenyl)imino)methyl)naphthalen-2-yl)oxy-κ2O,N)copper(II), C52H42CuN4O4
  13. Crystal structure of bis{5-(diethylamino)-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2O,N}cobalt(II), C40H38CoN4O6
  14. Crystal structure of diaqua-bis(N,N-dimethylformamide-κ1O)-bis{3-((5-chloro-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ4N,O,O′:O′}dinickel(II), C38H34Ni2Cl2N4O12
  15. Crystal structure of tetrakis(methanol-κO)bis{3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}bicobalt(II), C38H38Co2N2O14
  16. Crystal structure of (S)-tert-butyl-(1-hydroxypropan-2-yl)carbamate, C8H17NO3
  17. Crystal structure of 4-(4′-(pyridin-4-yl)-[1,1′-biphenyl]-4-yl)pyridin-1-ium catena-poly[{5-carboxy-4′-methyl-[1,1′-biphenyl]-3-carboxylato-κ2O,O′}-(μ2-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-κ4O,O′:O′′,O′′′)lead(II)], C52H40N2O9Pb
  18. Crystal structure of catena-poly[diaqua-(μ2-5-methylisophthalato-κ2O:O′)(μ2-1,4-bis((1H-1,2,4-triazol-1-yl)methyl)benzene-κ2N:N′)], NiC21H22O6N6
  19. Crystal structure of the salt tris(guanidinium) tris(tetrapropylammonium) bis(pyridine-2,4,6-tricarboxylate) – water (1/10), C55H126N14O22
  20. Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C19H18O8
  21. Crystal structure of poly{[μ2-1,1′-(sulfonylbis(4,1-phenylene))bis(2-methyl-1H-imidazole)-κ2N:N′][μ2-4,4′-oxydibenzoato-κ2O:O′]cobalt(II)} hemihydrate, C34H27N4O7.5SCo
  22. The crystal structure of 25,27-(2,2′-[(2-thioxo-1,3-dithiole-4,5-diyl)disulfanediyl]diethanolate)-26,28-dihydroxycalix[4]arene — dichloromethane (1/1), C36H32Cl2O4S5
  23. The crystal structure of 1,2-bis(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)ethane, C16H12N6O2
  24. Crystal structure of 1-benzyl-3-((4-bromophenyl)amino)-4-(4-methoxyphenyl)-1H-pyrrole-2,5-dione, C24H19BrN2O3
  25. Crystal structure of bis(2-((allylcarbamothioyl)imino)-4-methylthiazol-3-ido-κ2N,S)palladium(II), C16H20N6PdS4
  26. Crystal structure of pyrimidine-2,5-dicarboxylic acid 1.5 hydrate, C12H14N4O11
  27. Crystal structure of trans-diaqua-bis(1H-pyrazole-3-carboxylato-κ2N,O)manganese(II), C8H10N4O6Mn
  28. Crystal structure of catena-(μ3-5-bromoisophthatato-κO,O′: O′′,O′′′′)-(1,2-bis(imidazol-1-yl)ethane-κN:N′)cobalt(II), C16H13CoN4O4Br
  29. Investigation of the compound La5Zn2−xPb1 + x (x = 0.20–0.32)
  30. Crystal structure of (OC-6-13)-diaqua-bis(3,5-di(pyridin-3-yl)-4H-1,2,4-triazol-4-amine-κ1N)-bis(dicyanamido-κ1N)zinc(II) tetrahydrate, ZnC28H32N18O6
  31. Crystal structure of Ga0.62(3)Sb0.38(3)Pd3
  32. Crystal structure of Ga0.47(1)Sb0.53(1)Pd2
  33. A derivative of the Corey lactone – crystal structure of (3aR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate, C21H30O5Si
  34. A Corey lactone: crystal structure of (3aR,4R,5R,6aS)-5-benzoyloxy-4(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one, C15H16O5
  35. Hydrothermal synthesis and crystal structure of poly[aqua-(μ2-1,3-bis(4-pyridyl)propane-κ2N:N′)-(μ2-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylato-κ2O:O′)manganese(II) hydrate, C22H20Cl6N2O6Mn
  36. Crystal structure of 2-acetylpyrrole S-methylthiosemicarbazonium hydroiodide, C8H13IN4S
  37. Crystal structure of [N,N-bis((pyrrol-2-yl)ethylidene)butane-1,4-diamine-κ4N,N′,N′′,N′′′]-nickel(II), C16H20N4Ni
  38. Crystal structure of poly[aqua-(μ5-2,5-dicarboxybenzoato-κ5O:O:O′:O′′:O′′′)sodium(I)], C9H7NaO7
  39. Crystal structure of bis(N′-((1H-pyrrol-2-yl)methylene)-1-methylthio-methanethiohydrazido-κ2S,N)nickel(II), C14H16N6NiS4
  40. Crystal structure of 1-(4-((benzo[d][1,3]dioxol-5-yloxy)methyl)phenethyl)-4-(3-chlorophenyl) piperazin-1-ium chloride, C26H28Cl2N2O3
  41. Crystal structure of 2-(4-(2-(4-(2-fluorophenyl)piperazin-1-yl)ethyl)benzyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide, C26H26FN3O3S – a saccharin dervative
  42. Crystal structure of 3-(2-dimethylaminoethyl)-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C12H15N3OS
  43. Crystal structure of 3-(3-dimethylaminopropyl)-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C13H17N3OS
  44. The crystal structure of trans-tetraaqua-bis(p-tolylsulfinato-κO)calcium(II)), C14H22O8S2Ca
  45. The crystal structure of (E)-N′-(pyridin-2-ylmethylene)pyrazine-2-carbohydrazide, C11H9N5O
  46. Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C24H15NO
  47. Crystal structure of catena-poly[diaqua-(μ2-tartrato-κ4O,O′:O′′,O′′′)cobalt(II)], C4H8CoO8
  48. Crystal structure of 4-chloro-2-methyl-6-(4-(trifluoromethoxy)phenyl)pyrimidine, C12H8ClF3N2O
  49. Crystal structure of 1-(4-fluorophenyl)-N-(5-((triphenylstannyl)thio)thiophen-2-yl)methanimine, C27H20FN3S2Sn
  50. Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C10H8FN3OS2
  51. Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C22H31N5O4S2
  52. The crystal structure of (E)-2-((2-(o-tolylcarbamothioyl)hydrazono)methyl)benzoic acid, C16H15N3O2S
  53. Crystal structure of 2-chloro-1,3-di-tert-pentyl-4,4-diphenyl-1,3,2λ3,4-diazaphosphasiletidine, C22H32ClN2PSi
  54. Crystal structure of tetramethyl 5,5′-(buta-1,3-diyne-1,4-diyl)diisophthalate, C24H18O8
  55. Crystal structural of 2-amino-4-(4-methoxyphenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran, C19H20N2O3
  56. Crystal structure of 1,3,5-tris((trimethylsilyl)methyl)-1,3,5-triazinane-2,4,6-trione, C15H33N3O3Si3
  57. The crystal structure of bis(2-benzoyl-5-hydroxylphenolato-κ2O,O′)copper(II), C26H18CuO6
  58. Crystal structure of 2,6-bis(3-(pyrazin-2-yl)-1H-1,2,4-triazol-5-yl)pyridine – 1-ethyl-3-methyl-1H-imidazol-3-ium bromide (1/1), C23H22N13Br
  59. The crystal structure of (E)-N-benzyl-N′-benzylidene-4-methylbenzenesulfonohydrazide, C21H20N2O2S
  60. Crystal structure of ethyl (E)-5-((2-(3-hydroxybenzoyl)hydrazono)methyl)-3,4-dimethyl-1H-pyrrole-2-carboxylate – water – ethanol (1/1/1), C19H27N3O6
  61. The crystal structure of (E)-4-(3-ethoxy-2-hydroxybenzylideneamino)benzoic acid, C16H15NO4
  62. Crystal structure of (μ2-N,N′-bis((pyridin-4-yl)methyl)ethanediamide-κ2N:N′)-tetrakis(diethylcarbamodithioato-κ2S,S′)dizinc(II), C34H54N8O2S8Zn2
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