Home Crystal structure of 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]chinolizinium 3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate - methanol - water (1/1/1), C36H33NO10
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Crystal structure of 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]chinolizinium 3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate - methanol - water (1/1/1), C36H33NO10

  • Benyong Lou EMAIL logo , Yali Huang , Guocai Zheng and Qi Lin
Published/Copyright: September 13, 2017
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 232 Issue 6

Abstract

C36H33NO10, monoclinic, P21/c (no. 14), a = 14.113(7) Å, b = 17.883(9) Å, c = 12.724(7) Å, β = 108.218(9)°, V = 3050(3) Å3, Z = 4, Rgt(F) = 0.0788, wRref(F2) = 0.1967, T = 293 K.

CCDC no.:: 1511905

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

Table 1

Data collection and handling.

Crystal:Yellow needle
Size:0.25 × 0.10 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.0 cm−1
Diffractometer, scan mode:Rigaku CCD, φ and ω
2θmax, completeness:55°, >99%
N(hkl)measured, N(hkl)unique, Rint:23917, 6962, 0.071
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4866
N(param)refined:431
Programs:SHELXL [1], SHELXS [2], CrystalClear [3]
Table 2

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

AtomxyzUiso*/Ueq
O10.42164(12)0.24512(12)0.20957(14)0.0518(5)
O20.30277(13)0.17352(12)0.44727(15)0.0570(5)
O30.75058(12)0.23520(12)0.45429(16)0.0564(5)
O4−0.13952(12)0.26680(13)0.15280(17)0.0621(6)
H4A−0.17560.26960.08100.092(12)*
C10.32108(17)0.24258(16)0.1913(2)0.0454(6)
H10.27910.25790.12060.055*
C20.27671(16)0.22034(14)0.2648(2)0.0385(5)
C30.33839(17)0.19745(14)0.3758(2)0.0403(6)
C40.51573(17)0.19190(14)0.5023(2)0.0417(6)
H40.49270.17550.56100.050*
C50.61596(17)0.20205(15)0.5215(2)0.0427(6)
H50.66080.19300.59350.051*
C60.65442(17)0.22584(15)0.4359(2)0.0442(6)
C70.58559(18)0.23823(16)0.3308(2)0.0487(7)
H70.60820.25310.27110.058*
C80.48414(17)0.22872(15)0.3143(2)0.0419(6)
C90.44612(17)0.20522(14)0.3973(2)0.0384(5)
C100.16589(16)0.22497(14)0.2352(2)0.0389(5)
C110.12332(18)0.25365(17)0.3116(2)0.0488(7)
H110.16450.26500.38450.059*
C120.02116(18)0.26590(18)0.2825(2)0.0534(7)
H12−0.00650.28510.33610.064*
C130.10216(17)0.20658(15)0.1306(2)0.0437(6)
H130.12930.18520.07790.052*
C14−0.00044(18)0.21871(15)0.1013(2)0.0467(6)
H14−0.04240.20510.02970.056*
C15−0.04115(17)0.25072(16)0.1767(2)0.0447(6)
O50.50105(17)0.09294(15)0.9663(2)0.0802(7)
O60.33972(16)0.11788(14)0.96651(18)0.0722(6)
O70.01155(19)0.01491(17)0.1700(2)0.0910(8)
O8−0.17746(16)0.07326(14)0.12883(19)0.0785(7)
N10.20919(16)0.01588(13)0.48295(19)0.0487(6)
C160.4423(3)0.1162(2)1.0327(3)0.0743(9)
H16A0.46350.16661.06330.089*
H16B0.45140.08111.09520.089*
C170.4351(2)0.07959(17)0.8632(3)0.0584(8)
C180.3385(2)0.09456(16)0.8629(2)0.0530(7)
C190.2587(2)0.08551(15)0.7707(2)0.0500(7)
H190.19290.09560.77150.060*
C200.4557(2)0.05488(18)0.7716(3)0.0606(8)
H200.52220.04530.77280.073*
C210.37492(19)0.04414(16)0.6754(2)0.0497(7)
C220.27708(18)0.06057(14)0.6739(2)0.0453(6)
C250.19456(18)0.05670(14)0.5696(2)0.0441(6)
C230.3903(2)0.01558(19)0.5707(3)0.0604(8)
H23A0.39990.05830.52560.073*
H23B0.4511−0.01580.58930.073*
C240.3019(2)−0.02963(17)0.5053(3)0.0588(8)
H24A0.3110−0.04540.43450.071*
H24B0.2963−0.07510.54730.071*
C270.1423(2)0.01343(18)0.3836(2)0.0581(8)
H270.1577−0.01340.32650.070*
C280.0496(2)0.04898(16)0.3595(2)0.0520(7)
C290.02849(18)0.08746(14)0.4468(2)0.0457(6)
C260.10367(18)0.09205(15)0.5499(2)0.0465(6)
H260.09150.12030.60750.056*
C30−0.06731(19)0.12009(16)0.4241(3)0.0525(7)
H30−0.08420.14590.48100.063*
C31−0.13543(19)0.11472(16)0.3212(2)0.0537(7)
H31−0.19940.13660.30810.064*
C32−0.1137(2)0.07769(17)0.2339(3)0.0568(7)
C33−0.0209(2)0.04545(19)0.2525(3)0.0625(8)
C34−0.0362(4)−0.0445(3)0.1151(6)0.150(3)
H34A−0.0443−0.08190.16790.225*
H34B0.0024−0.06590.07050.225*
H34C−0.1020−0.02920.06650.225*
C35−0.2759(2)0.1020(2)0.1055(3)0.0816(11)
H35A−0.31080.07470.14910.122*
H35B−0.31190.09580.02650.122*
H35C−0.27270.15520.12470.122*
O100.6935(2)0.46124(16)0.2547(2)0.0876(8)
H10A0.74120.42020.28380.124(17)*
C360.7298(4)0.5193(3)0.3286(5)0.1184(17)
H36A0.79970.52890.33460.178*
H36B0.72500.50560.40130.178*
H36C0.69020.56450.30190.178*
O90.80292(17)0.33679(14)0.3239(2)0.0793(7)
H9A0.78060.30060.36010.129(18)*
H9B0.81710.31670.26980.096(14)*

Source of materials

A mixture of berberine chloride (370 mg, 1 mmol), NaOH (40 mg, 1 mmol) and daidzein (254 mg, 1 mmol) with 0.1 mL methanol added, was ground with a LAB WIZZ 320 ball mill in a 25 mL steel vessel for 15 min with a 15 mm steel ball at 30 Hz. The resulting powder was washed with water to remove the by-product NaCl and then re-crystallized in MeOH to give rise to yellow needle crystals.

Experimental details

The structure was solved by direct methods and refined on F2 by full-matrix least-squares methods using SHELXL [2]. H atoms on C atoms were located geometrically with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C). H atoms bonded to O were located by difference Fourier maps and the displacement factors were refined freely. Difference Fourier maps indicate disorder for one of the two methoxy groups, which could not be modelled satisfactorily against the available room-temperature data.

Comment

Flavonoids are a class of natural products with various pharmacological activities such as antioxidant and antitumor properties [4]. Multi-component crystals of flavonoids have been exploited recently [5]. Flavonoids have been also explored as cocrystal formers with other drug molecules [6].

Daidzein, 7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzo-pyran-4-one, is an isoflavone compound exhibiting a range of medicinal properties [7]. With two hydroxyl groups at opposite ends of the molecular structure it is a weak acid [8] capable of forming molecular salts and extended hydrogen-bonded structures. In this paper, we choose a basic natural product, berberine, as drug model. Daidzein crystallized in methanol with berberine to give rise to a 1:1:1 molecular salt hydrate, [C20H18NO4]+[C15H9O4]−⋅H2O⋅CH4O.

Difference Fourier maps show deprotonation of the 7-substituted hydroxyl group in the daidzein molecule. Hydrogen-bonded interactions between the resulting anion and 4′-substituted hydroxyl group [O4⋯O3], give rise to a 1D hydrogen-bonded chain along the [2 0 1] direction. The dihedral angle between the phenyl ring (C10—C15) and pyran ring (O1/C1—C2—C3/C8—C9) of daidzein is 41.14(7)°. The water molecule is hydrogen bonded to methanol and to O3 and O4 of the daidzein anion, thereby connecting the 1D chain into a 2D hydrogen-bonded layer. Berberine cations are located in between the 2D layers to give the host-guest arrays .

Acknowledgement

The authors are grateful to the grants from the Natural Science Foundation of Fujian Province (2015J01599; 2017J01584) and Research Project of Minjiang University (MYK16004).

References

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Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

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Received: 2017-3-22
Accepted: 2017-8-15
Published Online: 2017-9-13
Published in Print: 2017-11-27

©2017 Benyong Lou et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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  1. Cover and Frontmatter
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  6. Synthesis and crystal structure tetrakis(μ2-methanolato)-dimethanol-bis(μ2-2-acetyl-1,3-bis(3,5-dichloro-2-oxidophenyl)propane-1,3-bis(olato)-κ5O1,O2,O3:O3,O4,O5), tetramanganese(III), C40H40Cl8Mn4O16
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  65. The crystal structure of (E)-N′-(quinolin-2-ylmethylene)furan-2-carbohydrazide monohydrate, C15H13N3O3
  66. Crystal structure of 2,8-diphenyl-3,7,9-trioxa-1-azaspiro[4.5]dec-1-ene, C18H17N1O3
  67. Crystal structure of diethyl 2-(4-chlorophenyl)-1,3-dioxane-5,5-dicarboxylate, C16H19ClO6
  68. Crystal structure of 1-(carboxymethyl)-1H-benzo[d][1,2,3]triazole 3-oxide, C8H7N3O3
  69. Crystal structure of (acetylacetonato-κ2O,O′)-(2-amino-6-chlorobenzoato-κO)-oxido(1,10-phenanthroline-κ2N,N′)vanadium(IV) – trichloromethane (1/1)
  70. Crystal structure of (1E,4E)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one, C17H12Cl2O
  71. The crystal structure of trans-dibromido-bis(pyridine-κN)platinum(II), C10H10Br2N2Pt
https://doi.org/10.1515/ncrs-2017-0077
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of potassium 1-methyl-1H-1,2,3,4-tetrazole-5-thiolate, C2H3N4SK
  3. Crystal structure of bis(3-(3-ethylureido)-N,N-dimethylpropan-1-aminium) bis (μ3-2-(hydroxymethyl)-2-(oxidomethyl)propane-1,3-bis(olato))-(μ6-oxo)-hexakis(μ2-oxo)-hexaoxo-hexavanadium(V) – dichloromethane (1/1), C27H60Cl2N6O23V6
  4. Crystal structure of bis(μ3-methanolato-κ3O:O:O)-bis(μ2-methanolato-κ2O:O)-dimethanol-bis{6,6′-(1,3-dihydroxyl-2-acetylpropane-1,3-diyl)bis(2-chloro-4-bromophenolato)}tetramanganese(III) C40H40Br4Cl4Mn4O16
  5. Synthesis and crystal structure of tetrakis(μ2-methanolato)-dimethanol-bis(μ2-2-acetyl-1,3-bis(3,5-dibromo-2-oxidophenyl)propane-1,3-bis(olato)-κ5O1,O2,O3:O3,O4,O5)tetramanganese(III), C40H40Br8Mn4O16
  6. Synthesis and crystal structure tetrakis(μ2-methanolato)-dimethanol-bis(μ2-2-acetyl-1,3-bis(3,5-dichloro-2-oxidophenyl)propane-1,3-bis(olato)-κ5O1,O2,O3:O3,O4,O5), tetramanganese(III), C40H40Cl8Mn4O16
  7. Crystal structure of bis{5-methoxy-2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O)}copper(II), C34H34CuN4O6
  8. Crystal structure of (E)-1-(2-hydroxy-3-{[2-hydroxybenzylidene]amino}phenyl)ethan-1-one, C15H13NO3
  9. Crystal structure of bis(μ2-acetato-κ2O:O′)-bis{μ2-4-chloro-2-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ6O:O,N,N′,O′′:O′′}tricobalt(II), C44H49Cl2Co3N6O12
  10. Crystal structure of bis{μ2-2,4-dichloro-6-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ5O:O,N,N′,O′}dicobalt(II) acetone solvate, C43H48Br4Co2N6O9
  11. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-bis{μ2-4-chloro-2-(8-(4-(diethylamino)-2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)phenolato-κ6O:O,N,N′,O′:O′}trizinc(II), C44H49Cl2N6O12Zn3
  12. Crystal structure of bis{5-(N,N′-diethylamine)-5′-methoxy -2,2′-[ethylenediyldioxybis(nitrilomethylidyne)]diphenolato}-bis(μ2-acetato-κ2O:O′)trizinc(II), C46H56Zn3N6O14
  13. Crystal structure of tris(cyano-(hydrogen tris(3,5-dimethylpyrazolyl)borate))-iron(III) 4-methoxypyridinium monohydrate, C24H32BN10O2Fe
  14. Synthesis and crystal structure of bis{1-(((4-(1-(hydroxyimino)ethyl)phenyl)imino)methyl)naphthalen-2-olato-κ2O,N}copper(II), C38H30CuN4O4
  15. Crystal structure of (E)-1-(4-{[(E)-2-Hydroxy-1-naphthalenylmethylene] amino}phenyl)ethanone oxime, C19H16N2O2
  16. The pseudosymmetric crystal structure of 2-(2-naphthalenyl)-3-nitro-2H-1-benzopyran, C38H26N2O6
  17. Crystal structure of 2-benzoyl-3-(4-methoxyphenyl)cyclopropane-1,1-dicarbonitrile, C19H14N2O2
  18. N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide monohydrate, C17H21N3O5
  19. The crystal structure of carbonyl-[4-(2,4-dichlorophenylamino)pent-3-en-2-onato-κ2N,O]-(triphenylphosphine-κP)rhodium(I), RhC30H25Cl2NO2P
  20. Crystal structure of (E)-5-(diethylamino)-2-(((1,1,2-trihydroxyethyl)iminio)methyl)phenolate, C15H24N2O4
  21. Crystal structure of poly[(μ2-1,4-bis((2-ethyl-1H-benzo[d]imidazol-1-yl)methyl)benzene-κ2N:N′)(μ2-isophthalato-κ4O,O′:O′′,O′′′)cadmium(II)], C34H30N4O4Cd
  22. Crystal structure of 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]chinolizinium 3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate - methanol - water (1/1/1), C36H33NO10
  23. A single crystal study on 2-(methylcarbamoyl)benzoic acid, C9H9NO3
  24. Crystal structure of the salt 1,1′-(ethane-1,2-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) diperchlorate, C14H28N4(ClO4)2
  25. Crystal structure of 2,5-bis((E)-2-(trifluoromethyl)benzylidene)cyclopentan-1-one, C21H14F6O
  26. Crystal structure of catena-poly[(μ2-benzene-1,4-dicarboxylato-κ2O:O′)-(1-ethyl-6-fluoro-7-(4-methylpiperazin-1-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylato-κ2O,O′)zinc(II)] 1.25 hydrate, C25H26.5N3O8.25FZn
  27. Crystal structure of 1-methyl-1,4-diazabicyclo[2.2.2]octan-1-ium poly[aqua-bis(μ2-perchlorato-κ3O,O′:O′′)sodium], C7H17Cl2N2NaO9
  28. Crystal structure of trimethyammonium 2,6-dicarboxyisonicotinate monohydrate, C11H16N2O7
  29. Crystal structure of dodecaguanidinium bis(tetrapropylammonium) heptacarbonate, C43H128N38O21
  30. Crystal structure of poly[tetraaqua-bis(μ6-benzene-1,2,4,5-tetracarboxylato)nickel(II)diyttrium(III)]dihydrate, C20H16NiO22Y2
  31. Halogen bonds and π–π interactions in the crystal structure of 1,3,5-trifluoro-2,4,6-triiodobenzene–N,N-dimethylformamide (1/1), C9H7F3I3NO
  32. Crystal structure of guanidinium tetraethylammonium carbonate dihydrate, C10H30N4O5
  33. The crystal structure of oxonium chlorido-ethylenediaminetetraactetotin(IV) hydrate, C10H17ClN2O10Sn
  34. Crystal structure of 8-((E)-((4-((E)-1-((benzyloxy)imino)ethyl)phenyl)imino)methyl)-7-hydroxy-4-methyl-2H-chromen-2-one, C26H22N2O4
  35. Crystal structure of bis{5-(diethylamino)-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2O,N}copper(II), C40H38CuN4O6
  36. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(tri(p-tolyl)phosphine-κP)rhenium(I), C29H28O5PRe
  37. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl(benzyldiphenylphosphine-κP)rhenium(I), C27H24O5PRe
  38. Crystal structure of triethylammonium bis{3-(((3-oxidonaphthalen-1-yl)methylene)amino)-2-oxo-2H-chromen-4-olato-κ3O,N,O′}manganese(III), C46H38MnN3O8
  39. Crystal structure of bis(N,N,N-ethyldimethylethanaminium) bis(heptaselenido-κ2Se1,Se7)palladate(II), C12H32N2PdSe14
  40. Crystal structure of bis(4-(1H-pyrazol-5-yl)pyridine-κ2N:N′)-bis(2-(2-((2,6-difluorophenyl)amino)phenyl)acetate-κO)cadmium(II), C44H34N8CdCl4O4
  41. Crystal structure of 4,4′-(1,4-phenylene)bis(pyridin-1-ium) catena-poly[diaqua-bis(μ2-3′,5′-dicarboxy-[1,1′-biphenyl]-2,5-dicarboxylato-κ2O:O′] dihydrate, C48H42O22N2Ca
  42. The crystal structure of (S)-2-benzylsuccinic acid, C11H12O4
  43. Crystal structure of poly[aqua-(μ3-4-(pyridin-4-yl)isophthalato-κ4O,O′:O′′:O′′′)-(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:O′)yttrium(III)], C26H17N2O9Y
  44. Crystal structure of ethyl 1-(3,4-dimethylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylate, C14H17N3O2
  45. Crystal structure of tetrakis(methanol-κO)-bis{μ2-3-((4-methoxy-2-oxidobenzylidene)amino)-2-oxo-2H-chromen-4-olate-κ4O,N;O′:O′}dizinc(II), C38H38Zn2N2O14
  46. Crystal structure of bromido(4,4′-dimethoxy-2,2′-bipyridine-κ2N,N′)(isopropyl(diphenyl)phosphane-κP)copper(I), C27H29BrCuN2O2P
  47. Crystal structure of bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-9,9-dioctylfluorene, C41H64B2O4
  48. Crystal structure of 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carbaldehyde - a julolidine derivative, C16H15NO3
  49. Crystal structure of 1,3-dimethyl-5,5-dibenzylbarbituric acid, C20H20N2O3
  50. Crystal structure of bis(N,N,N-trimethylethanaminium) poly[bis(μ2-heptaselenido-κ2Se1,Se7)palladate(II)], C10H28N2PdSe14
  51. Crystal structure of 1-{4-[(5-Chloro-2-hydroxy-benzylidene)amino]phenyl} ethanone O-ethyl-oxime, C17H17ClN2O2
  52. The crystal structure of methyl N-(4-bromophenyl)carbamate, C8H8BrNO2
  53. Synthesis and crystal structure of 1-{4-[(2-hydroxy-benzylidene)amino]phenyl}ethanone oxime, C15H14N2O2
  54. Crystal structure of 1,1′-butanebis(3-methyl-1H-imidazol-3-ium)bis(hexafluorophosphate), C12H20F12N4P2
  55. (E)-N-benzylidene-3-(benzylthio)-5-p-tolyl-4H-1,2,4-triazol-4-amine, C23H20N4S
  56. Crystal structure of ethyl 5-methyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate, C11H12N4O2
  57. Crystal structure of 5,5-difluoro-10-(4-fluorophenyl)-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine - a Z′ = 3 structure, C19H18B2F3N2
  58. The crystal structure of the Matrine derivative: 12-(1H-indol-1-yl)dodecahydro-1H,5H,10H-dipyrido[2,1-f:3′,2′,1′-ij][1,6]naphthyridin-10-one hydrate, C23H29N3O
  59. The crystal structure of tris(μ2-1,3-bis(4,4,4-trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-κ2O,O′)dilutetium(III), C50H38F18Lu2O16
  60. The crystal structure of (Z)-2-(3-(2-(4-chlorobenzoyl)hydrazono)-2-oxoindolin-1-yl) acetic acid, C17H12ClN3O4
  61. Synthesis and crystal structure of trans-tetraqua-bis(2-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)acetato-κO)cobalt(II) hexahydrate, C36H48CoN2O28S2
  62. The crystal structure of N,N-dimethyl-2,6-di-p-tolylpyrimidin-4-amine, C20H21N3
  63. The crystal structure (E)-4-methyl-N′-(2-nitrobenzylidene)benzenesulfonohydrazide, C14H13N3O4S
  64. Crystal structure of catena-poly[(μ2-1,3-bis(benzimidazol-1-yl)propane κ2N:N′)-(μ2-5-methoxyisophthalato-κ2O:O′)zinc(II)] hydrate, C26H24ZnN4O6
  65. The crystal structure of (E)-N′-(quinolin-2-ylmethylene)furan-2-carbohydrazide monohydrate, C15H13N3O3
  66. Crystal structure of 2,8-diphenyl-3,7,9-trioxa-1-azaspiro[4.5]dec-1-ene, C18H17N1O3
  67. Crystal structure of diethyl 2-(4-chlorophenyl)-1,3-dioxane-5,5-dicarboxylate, C16H19ClO6
  68. Crystal structure of 1-(carboxymethyl)-1H-benzo[d][1,2,3]triazole 3-oxide, C8H7N3O3
  69. Crystal structure of (acetylacetonato-κ2O,O′)-(2-amino-6-chlorobenzoato-κO)-oxido(1,10-phenanthroline-κ2N,N′)vanadium(IV) – trichloromethane (1/1)
  70. Crystal structure of (1E,4E)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one, C17H12Cl2O
  71. The crystal structure of trans-dibromido-bis(pyridine-κN)platinum(II), C10H10Br2N2Pt
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