Home Physical Sciences Crystal structure of 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate methanol solvate, C37H35N1O10
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Crystal structure of 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate methanol solvate, C37H35N1O10

  • Yanjie Zhang , Benyong Lou EMAIL logo , Yali Huang , Guocai Zheng and Qi Lin
Published/Copyright: May 26, 2017
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 232 Issue 4

Abstract

C37H35N1O10, triclinic, P1̅ (no. 2), a = 12.039(8) Å, b = 12.353(9) Å, c = 12.938(9) Å, α = 102.786(3)°, β = 111.865(6)°, γ = 105.173(7)°, V = 1610.6(19) Å3, Z = 2, Rgt(F) = 0.0567, wRref(F2) = 0.1392, T = 293 K.

CCDC no.:: 1547648

The asymmetric unit of 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 prism
Size:0.40 × 0.20 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.0 cm−1
Diffractometer, scan mode:Rigaku CCD, profile fitting-scans
2θmax, completeness:55°, >98%
N(hkl)measured, N(hkl)unique, Rint:17459, 7338, 0.037
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4463
N(param)refined:450
Programs:SHELX [1], CrystalClear [2]
Table 2

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

AtomxyzUiso*/Ueq
O10.19705(15)0.41866(12)−0.04936(11)0.0497(4)
O20.16415(16)0.11830(13)0.04068(13)0.0571(4)
O30.10360(15)−0.00479(12)−0.17636(13)0.0508(4)
O40.08866(14)0.20298(13)−0.44399(11)0.0520(4)
O50.24153(17)0.39868(16)0.55828(12)0.0626(4)
O60.20665(14)−0.22059(13)−0.08053(13)0.0586(4)
O70.38751(17)−0.25844(16)−0.14829(14)0.0730(5)
O80.56395(14)0.32428(13)0.81085(13)0.0576(4)
O90.75132(13)0.32190(13)0.76184(13)0.0611(4)
O10−0.15321(19)0.2125(2)−0.53819(18)0.0884(6)
N10.31940(16)0.00540(15)0.25674(15)0.0459(4)
C10.2090(2)0.42017(18)0.05954(17)0.0449(5)
H10.22640.49320.11410.054*
C20.19792(18)0.32621(16)0.09530(16)0.0377(4)
C30.16968(18)0.20967(17)0.01147(16)0.0382(4)
C40.11751(17)0.09892(16)−0.19870(16)0.0366(4)
C50.09717(18)0.09813(17)−0.31065(16)0.0398(4)
H50.07490.0265−0.36990.048*
C60.10948(18)0.20442(18)−0.33766(16)0.0399(5)
C70.14537(19)0.31216(18)−0.24516(17)0.0418(5)
H70.15590.3837−0.25960.050*
C80.16454(18)0.31098(16)−0.13445(16)0.0366(4)
C90.15081(17)0.20653(16)−0.10553(15)0.0344(4)
C100.21225(19)0.34236(17)0.21779(16)0.0384(4)
C110.3143(2)0.43618(19)0.31671(17)0.0510(5)
H110.37830.48770.30710.061*
C120.3234(2)0.4552(2)0.42972(18)0.0548(6)
H120.39240.51930.49460.066*
C130.1180(2)0.26720(17)0.23567(17)0.0421(5)
H130.04810.20380.17060.051*
C140.1260(2)0.28476(18)0.34761(17)0.0445(5)
H140.06190.23350.35730.053*
C150.2296(2)0.37864(18)0.44597(17)0.0455(5)
C160.1529(3)−0.3471(2)−0.1092(3)0.0916(10)
H16A0.1697−0.3641−0.03720.137*
H16B0.1916−0.3854−0.15090.137*
H16C0.0611−0.3770−0.15880.137*
C170.4771(3)−0.2955(3)−0.1794(2)0.0863(9)
H17A0.5202−0.3285−0.12340.130*
H17B0.5398−0.2276−0.17760.130*
H17C0.4315−0.3553−0.25800.130*
C180.4303(2)−0.18132(19)−0.03613(19)0.0529(6)
C190.3368(2)−0.16566(18)−0.00399(19)0.0488(5)
C200.3753(2)−0.08678(18)0.11117(18)0.0445(5)
C210.5622(2)−0.1159(2)0.04518(19)0.0541(6)
H210.6245−0.12460.02170.065*
C220.6011(2)−0.04013(19)0.15723(19)0.0516(5)
H220.68890.00120.20910.062*
C230.50826(19)−0.02451(17)0.19458(18)0.0436(5)
C240.54026(19)0.04635(17)0.31044(18)0.0437(5)
H240.62700.08490.36620.052*
C250.2847(2)−0.06515(18)0.14712(19)0.0474(5)
H250.1974−0.10130.09260.057*
C260.44834(18)0.06076(17)0.34425(18)0.0416(5)
C270.47484(18)0.12917(16)0.46515(17)0.0405(5)
C280.37452(19)0.12398(17)0.49562(19)0.0446(5)
C290.2379(2)0.0440(2)0.4047(2)0.0557(6)
H29A0.2194−0.03580.40880.067*
H29B0.17840.07520.42230.067*
C300.2183(2)0.0369(2)0.2818(2)0.0608(6)
H30A0.1336−0.02320.22390.073*
H30B0.22120.11360.27350.073*
C310.4021(2)0.18956(18)0.61024(19)0.0472(5)
H310.33450.18810.62910.057*
C320.60373(19)0.19681(17)0.55377(18)0.0454(5)
H320.67140.20080.53450.054*
C330.62982(19)0.25668(17)0.66815(19)0.0449(5)
C340.5277(2)0.25674(17)0.69648(19)0.0450(5)
C350.4659(2)0.3534(2)0.8348(2)0.0679(7)
H35A0.40310.28200.82770.102*
H35B0.42420.38680.77860.102*
H35C0.50500.41080.91410.102*
C360.8588(2)0.3396(3)0.7370(2)0.0913(10)
H36A0.85120.38160.68220.137*
H36B0.86040.26310.70250.137*
H36C0.93730.38580.80970.137*
C37−0.1391(4)0.3170(4)−0.5668(3)0.1244(14)
H37A−0.20600.3444−0.56420.187*
H37B−0.14560.2997−0.64540.187*
H37C−0.05600.3783−0.51020.187*
H30.124(3)0.025(2)−0.092(2)0.088(9)*
H10−0.069(3)0.205(3)−0.513(3)0.117(11)*
H5A0.179(3)0.324(3)0.555(3)0.111(11)*

Source of material

Palmatine chloride (systematic name: 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium chloride; 387 mg, 1 mmol) was dissolved in absolute methanol (30 mL) and NaOH (40 mg, 1 mmol) was added under stirring conditions. Genistein (systematic name: 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one; 270 mg, 1 mmol) was then added. The mixture was stirred for 8 h and then filtered. The yellow powder was further recrystallized in absolute methanol and yellow block crystals were obtained after several days.

Experimental details

The structure was solved by direct methods and refined on F2 by full-matrix least-squares methods using the SHELXTL program package [1]. Hydrogen atoms bound to carbon atoms were located geometrically with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C). Hydrogen atoms bonded to oxygen were located by difference maps and the displacement factors were freely refined.

Discussion

Drug-drug molecular salts have been exploited as new crystal forms of active pharmaceutical ingredients [3]. Flavonoids are natural occurring polyphenolic compounds with health-prolonging effects such as antioxidant, antitumor and anti-inflammatory properties [4]. Genistein, a soy isoflavone, could enhance anti-cancer effects [5]. There are three hydroxyl groups in molecular structure of genistein in 5, 7 and 4′ positions, respectively. The hydroxyl group in the 7 position may easily lose its proton under basic conditions. Palmatine, a natural alkaloid, has antioxidant and anti-inflammatory properties [6]. Salt formation of palmatine and genistein gave rise to a 1:1 compound.

The title compound crystallizes in the triclinic space group P1̅ and contains one deprotonated genistein anion, one palmatine cation and one methanol in the asymmetric unit. Genistein lost its proton in 7-substituted hydroxyl O4 to become the genistein anion (cf. the figure). The hydroxyl group O3 is involved in intramolecular hydrogen-bonding interactions with O2 of —C = O group [O3…O2 = 2.595(3) Å]. O5 is involved in hydrogen bond with the phenolic anion [O5…O4A = 2.614(3) Å, A = x, y, z + 1], which resulted in an 1D hydrogen-bonded chain of genistein anion along the c axis. There is a dihedral angel of 49.11(7)° between the phenyl moiety (C10—C15) and pyran moiety (O1/C1—C2—C3/C8—C9) of genistein. There also exist hydrogen-bonding interactions between methanol and O4 of genistein anion [O10…O4 = 2.753(3) Å].

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 21503105

Funding source: Natural Science Foundation of Fujian Province

Award Identifier / Grant number: 2015J01599

Funding statement: The authors are grateful to the grants from the National Natural Science Foundation of China (21503105), the Natural Science Foundation of Fujian Province (2015J01599) and Research Project of Minjiang University (MYK16004).

References

1 Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

2 Rigaku/MSC. CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA, 2000.Search in Google Scholar

3 Thorat, S. H.; Sahu, S. K.; Patwadkar, M. V.; Badiger, M. V.; Gonnade, R. G.: Drug-drug molecular salt hydrate of an anticancer drug gefitinib and a loop diuretic drug furosemide: an alternative for multidrug treatment. J. Pharm. Sci. 104 (2015) 4207–4216.10.1002/jps.24651Search in Google Scholar PubMed

4 Crozier, A.; Jaganath, I. B.; Clifford, M. N.: Dietaryphenolics: chemistry, bioavailability and effects on health. Nat. Prod. Rep. 26 (2009) 1001–1043.10.1039/b802662aSearch in Google Scholar PubMed

5 Zhou, R. J.; Yang, X. Q.; Wang, D.; Zhou, Q.; Xia, L.; Li, M. X.; Zeng, L. L.; Wang, G.; Yang, Z. Z.: Anti-tumor effects of all-trans retinoic acid are enhenced by genistein. Cell. Biochem. Biophys. 62 (2012) 177–184.10.1007/s12013-011-9279-0Search in Google Scholar PubMed

6 Kim, Y. M.; Ha, Y. M.; Jin, Y. C.; Shi, L. Y.; Lee, Y. S.; Kim, H. J.; Seo, H. G.; Choi, J. S.; Kim, Y. S.; Kang, S. S.: Palmatine from coptidis rhizoma reduces ischemia-reperfusion-mediated acute myocardial injury in the rat. Food. Chem. Toxicol. 47 (2009) 2097–2102.10.1016/j.fct.2009.05.031Search in Google Scholar PubMed

Received: 2016-12-31
Accepted: 2017-5-3
Published Online: 2017-5-26
Published in Print: 2017-7-26

©2017 Yanjie Zhang et al., published by De Gruyter, Berlin/Boston.

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

Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)manganese(II)] bis(4-chlorobenzenesulfonate) – 4,4′-bipyridine – water (1/1/2) C42H40Cl2MnN6O10S2
  3. The crystal structure of 1,2-bis[2-methyl-5-(3-cyanophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H16F6N2S2
  4. Crystal structure of the first characterized polymeric copper and sodium complex diaqua-(tris-acetato-κO,O′)(μ2-acetato-κO′′)dinatrium copper(II) monohydrate, C8H18CuNa2O11
  5. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-3-yl-methylene)aniline, C18H22N2
  6. Crystal structure of methyl 2,7,7-trimethyl-4-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C20H22N2O5
  7. Crystal structure of bis(1,3-bis(diphenylphosphino)propane-κ2P,P′)silver(I) trifluorosulfonate–methanol (1:0.5), [Ag(C27H26P2)]SO3CF3⋅0.5CH3OH
  8. Crystal structure of μ-1,4-bis(diphenylphosphine)butane-2,9-dimethyl-1,10-phenanthroline-κ2N:N′-bis(cyano-κC)dicopper(I)]-water, C58H56Cu2N6O2P2
  9. Crystal structure of N2,N6-bis(1-hydrazinyl-2-methyl-1-oxopropan-2-yl) pyridine-2,6-dicarboxamide, C15H23N7O4
  10. Crystal structure of 1,3-dimethyl-2-phenyl-1H-perimidin-3-ium iodide, C19H17IN2
  11. Crystal structure of diaqua-(2,2′-(butane-1,4-diyl)-bis(5-carboxy-1H-imidazole-4-carboxylato)-κ4O,O′,N,N′)cadmium(II) monohydrate, C14H18O11N4Cd
  12. Crystal structure of ethyl (E)-3-(cyclopropylamino)-2-(2,4-dichloro-5-fluorobenzoyl) acrylate, C15H14Cl2FNO3
  13. Crystal structure of bis-(1-(4-chlorophenyl)-3-phenyl-4-thenoyl-1H-pyrazol-5-ol-κ2O,O′)-(N,N-dimethylformamide)zinc(II), C43H31Cl2N5O5S2Zn
  14. Crystal structure of tetrakis(μ3-2-(N-(2-hydroxyethyl)amino)ethoxo)-tetrachloro-tetra-cobalt(II) methanol solvate, C17H44Cl4Co4N4O9
  15. Crystal structure of 3-amino-1-(4-bromophenyl)-9-methoxy-1H-benzo[f]chromene-2-carbonitrile, C21H15BrN2O2
  16. Crystal structure of 2-amino-4-(4-isopropyl-phenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene, C22H18N2O3
  17. Crystal structure of 3-amino-8-methoxy-1-(4-methoxy phenyl)-1H-benzo[f]chromene-2-carbonitrile, C22H18N2O3
  18. Crystal structure of monoaqua-[6,6′-((1E,1′E)-(1,2-phenylene bis(azanylylidene))bis(methanylylidene))bis(4-bromo-2-nitrophenolato-κ4N,N′,O,O′)]zinc(II), C20H12Br2N4O7Zn
  19. Crystal structure of 11-(4-(dimethylamino)phenyl)-17-hydroxy-13-methyl-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one – acetonitril (1/2), C33H41N3O2
  20. Crystal structure of tert-butyl (phenylsulfinyl)carbamate, C11H15NO3S
  21. Crystal structure of catena-poly{diaqua-bis(3-(1H-1,2,4-triazol-1-yl)benzoato-κ2O:N)copper(II)} monohydrate, C18H18CuN6O7
  22. Crystal structure of tetraaqua-bis(3-(4H-1,2,4-triazol-4-yl)benzoato-κN)cobalt(II), C18H20CoN6O8
  23. The crystal structure of 4-bromo-N-cyclopropyl-2,5-difluorobenzenesulfonamide, C9H8BrF2NO2S
  24. Crystal structure of ([3,3′-bipyridine]-6,6′-dicarboxylato-κ2O:O′)-bis(1,2-bis(4-pyridyl)ethane-κ2N:N′)disilver(I) dihydrate, C37H35Ag2N5O6
  25. The crystal structure of (4-(1H-1,2,4-triazol-1-yl)benzoato-κN)-[4-(1H-1,2,4-triazol-1-yl)benzoic acid-κN]silver(I), C18H13AgN6O4
  26. Crystal structure of 3-(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one, C17H16O2
  27. Crystal structure of bis(2-((E)-((4-((E)-1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-methoxyphenolato-κ2O,N)copper(II), C36H38CuN4O6
  28. Crystal structure of poly[1,2-bis(1,2,4-triazol-4-yl)ethane-κ2N:N′]silver(I) bromate monohydrate]silver(I), C6H10AgBrN6O4
  29. The crystal structure of 2,3,5-triphenyl-2,3-dihydro-1H-tetrazol-1-ium 2,3-dioxoindoline-5-sulfonate, C27H19N5O5S
  30. Crystal structure of 3-(2-amino-1,3-selenazol-4-yl)-2H-chromen-2-one – dimethylformamide (1/1), C15H15N3O3Se
  31. Crystal structure of diethyl 3,3′-(diazene-1,2-diyl)(E)-dibenzoate, C18H18N2O4
  32. Crystal structure of cis-bis((1H-benzimidazol-2-yl)methanol-κN,O)-bis(isothiocyanato-κN)nickel(II), C18H16N6NiO2S2
  33. Crystal structure of bis(2-(2′-hydroxy-5′-methoxyphenyl)-1H-benzimidazole)boron – tetrahydrofuran (1/1), C36H37N4O6B
  34. Crystal structure of poly[aqua-bis(nitrato-κ2O,O′)-(μ3-1,3-benzimidazol-3-ium-1,3-diacetato-κ4O,O′:O′′:O′′′)dysprosium(III)], C11H11DyN4O11
  35. Crystal structure of n-butyl-tris(dicyclo-hexylamido)hafnium(IV), C40H75HfN3
  36. Crystal structure of (E)-1-[1-(3-chloro-4-fluoro-phenyl)ethylidene]-2-(2,4-dinitrophenyl)hydrazine, C28H20Cl2F2N8O8
  37. The crystal structure of ethyl 4-((2-hydroxybenzyl)amino)benzoate, a Schiff base, C16H17NO3
  38. Crystal structure of 3-(2-(4-isobutylphenyl)propanoyl)-1-methylimidazolidine-2,4-dione, C17H22N2O3
  39. Crystal structure of poly[(μ3-2-(pyrazin-2-ylthio)acetato-κ3N:O:S)silver(I)], C6H5AgN2O2S
  40. Crystal structure of (E)-1-(3-((E)-((2-hydroxynaphthalen-1-yl)methylene)amino)phenyl)ethanone O-benzyl oxime, C26H22N2O2
  41. Crystal structure of (E)-2,3-dihydroxybenzaldehyde O-(2-((((E)-1-(2,5-dihydroxyphenyl)ethylidene)amino)oxy)ethyl) oxime monohydrate, C17H20N2O7
  42. Crystal structure of 4-(chloromethyl)-3-nitrobenzoic acid, C8H6ClNO4
  43. Crystal stucture of 4-((10H-phenothiazin-10-yl)methyl)-2,6-di-tert-butylphenol, C27H31NOS
  44. The crystal structure of ethyl 1-(4-nitrophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C13H10F3N3O4
  45. Crystal structure of catena-poly[di-(μ3-oxido-κ3O:O:O)-tetraoxido-(μ2-5′-(pyrazin-2-yl)-1H,2′H-3,3′-bi(1,2,4-triazole)-κ2N:N′)dimolybdenum(VI)], C8H6Mo2N8O6
  46. Crystal structure of (3,6-dioxocyclohexa-1,4-diene-1,4-bis(olato)-κ4O,O′:O′′,O′′′)-bis(tris(2-pyridylmethyl)amine-κ4N,N′,N′′,N′′′))-dizinc(II) bis(hexafluorophosphate(V)), C42H38F12N8O4P2Zn2
  47. Crystal structure of catena-poly[hexakis(μ2-2-acetylphenolato-κ3O:O,O′)trimanganese(II)], C48H42Mn3O12
  48. The crystal structure of 2,2-difluoro-4-(trifluoromethyl)-2,5-dihydro-[1,3,2]dioxaborinino[5,4-c]chromen-3-ium-2-uide, C11H6BF5O3
  49. Crystal structure of methyl (E)-2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazine-1-carboxylate, C13H19N3O3
  50. The crystal structure of tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate, C10H15N3O2
  51. Crystal structure of 1,1-bis(η5-adamantylcyclopentadienyl)-3-phenyl-2-trimethylsilyl-2,3-dihydroisotitanazole, C42H55NSiTi
  52. Crystal structure of 2-(4-(2-(4-benzylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C28H29N3O2
  53. Important impurity of Flupirtine – a single crystal study on ethyl (6-amino-5-((ethoxycarbonyl)amino)pyridin-2-yl)(4-fluorobenzyl)carbamate, C18H21FN4O4
  54. Crystal structure of ethyl 3-(4-methoxyphenyl)-1-(2-(4-methoxyphenyl)-2-oxoethyl)-1H-pyrazole-5-carboxylate, C22H22N2O5
  55. Crystal structure of 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate methanol solvate, C37H35N1O10
  56. The crystal structure of the inner salt of 2-[(aminoiminomethyl)amino]ethylcarbamic acid [systematic name: (2-((diaminomethylene)ammonio)ethyl)carbamate], C4H10N4O2
  57. Crystal structure of (8-hydroxy-5-nitroquinolinium) perchlorate – 8-hydroxy-5-nitroquinoline (1/1), C18H13ClN4O10
  58. The crystal structure of (5-methyl-1,2,4-oxadiazol-3-yl)ferrocene, C13H12FeN2O
  59. Crystal structure of methyl 1-(2-(fluorosulfonyl)ethyl)-2-oxocyclopentanecarboxylate, C9H13FO5S
  60. Crystal structure of the triclinic modification of 1-methyl-4-nitroimidzole, C4H5N3O2
  61. Corrigendum
  62. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
https://doi.org/10.1515/ncrs-2016-0412
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)manganese(II)] bis(4-chlorobenzenesulfonate) – 4,4′-bipyridine – water (1/1/2) C42H40Cl2MnN6O10S2
  3. The crystal structure of 1,2-bis[2-methyl-5-(3-cyanophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H16F6N2S2
  4. Crystal structure of the first characterized polymeric copper and sodium complex diaqua-(tris-acetato-κO,O′)(μ2-acetato-κO′′)dinatrium copper(II) monohydrate, C8H18CuNa2O11
  5. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-3-yl-methylene)aniline, C18H22N2
  6. Crystal structure of methyl 2,7,7-trimethyl-4-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C20H22N2O5
  7. Crystal structure of bis(1,3-bis(diphenylphosphino)propane-κ2P,P′)silver(I) trifluorosulfonate–methanol (1:0.5), [Ag(C27H26P2)]SO3CF3⋅0.5CH3OH
  8. Crystal structure of μ-1,4-bis(diphenylphosphine)butane-2,9-dimethyl-1,10-phenanthroline-κ2N:N′-bis(cyano-κC)dicopper(I)]-water, C58H56Cu2N6O2P2
  9. Crystal structure of N2,N6-bis(1-hydrazinyl-2-methyl-1-oxopropan-2-yl) pyridine-2,6-dicarboxamide, C15H23N7O4
  10. Crystal structure of 1,3-dimethyl-2-phenyl-1H-perimidin-3-ium iodide, C19H17IN2
  11. Crystal structure of diaqua-(2,2′-(butane-1,4-diyl)-bis(5-carboxy-1H-imidazole-4-carboxylato)-κ4O,O′,N,N′)cadmium(II) monohydrate, C14H18O11N4Cd
  12. Crystal structure of ethyl (E)-3-(cyclopropylamino)-2-(2,4-dichloro-5-fluorobenzoyl) acrylate, C15H14Cl2FNO3
  13. Crystal structure of bis-(1-(4-chlorophenyl)-3-phenyl-4-thenoyl-1H-pyrazol-5-ol-κ2O,O′)-(N,N-dimethylformamide)zinc(II), C43H31Cl2N5O5S2Zn
  14. Crystal structure of tetrakis(μ3-2-(N-(2-hydroxyethyl)amino)ethoxo)-tetrachloro-tetra-cobalt(II) methanol solvate, C17H44Cl4Co4N4O9
  15. Crystal structure of 3-amino-1-(4-bromophenyl)-9-methoxy-1H-benzo[f]chromene-2-carbonitrile, C21H15BrN2O2
  16. Crystal structure of 2-amino-4-(4-isopropyl-phenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene, C22H18N2O3
  17. Crystal structure of 3-amino-8-methoxy-1-(4-methoxy phenyl)-1H-benzo[f]chromene-2-carbonitrile, C22H18N2O3
  18. Crystal structure of monoaqua-[6,6′-((1E,1′E)-(1,2-phenylene bis(azanylylidene))bis(methanylylidene))bis(4-bromo-2-nitrophenolato-κ4N,N′,O,O′)]zinc(II), C20H12Br2N4O7Zn
  19. Crystal structure of 11-(4-(dimethylamino)phenyl)-17-hydroxy-13-methyl-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one – acetonitril (1/2), C33H41N3O2
  20. Crystal structure of tert-butyl (phenylsulfinyl)carbamate, C11H15NO3S
  21. Crystal structure of catena-poly{diaqua-bis(3-(1H-1,2,4-triazol-1-yl)benzoato-κ2O:N)copper(II)} monohydrate, C18H18CuN6O7
  22. Crystal structure of tetraaqua-bis(3-(4H-1,2,4-triazol-4-yl)benzoato-κN)cobalt(II), C18H20CoN6O8
  23. The crystal structure of 4-bromo-N-cyclopropyl-2,5-difluorobenzenesulfonamide, C9H8BrF2NO2S
  24. Crystal structure of ([3,3′-bipyridine]-6,6′-dicarboxylato-κ2O:O′)-bis(1,2-bis(4-pyridyl)ethane-κ2N:N′)disilver(I) dihydrate, C37H35Ag2N5O6
  25. The crystal structure of (4-(1H-1,2,4-triazol-1-yl)benzoato-κN)-[4-(1H-1,2,4-triazol-1-yl)benzoic acid-κN]silver(I), C18H13AgN6O4
  26. Crystal structure of 3-(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one, C17H16O2
  27. Crystal structure of bis(2-((E)-((4-((E)-1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-methoxyphenolato-κ2O,N)copper(II), C36H38CuN4O6
  28. Crystal structure of poly[1,2-bis(1,2,4-triazol-4-yl)ethane-κ2N:N′]silver(I) bromate monohydrate]silver(I), C6H10AgBrN6O4
  29. The crystal structure of 2,3,5-triphenyl-2,3-dihydro-1H-tetrazol-1-ium 2,3-dioxoindoline-5-sulfonate, C27H19N5O5S
  30. Crystal structure of 3-(2-amino-1,3-selenazol-4-yl)-2H-chromen-2-one – dimethylformamide (1/1), C15H15N3O3Se
  31. Crystal structure of diethyl 3,3′-(diazene-1,2-diyl)(E)-dibenzoate, C18H18N2O4
  32. Crystal structure of cis-bis((1H-benzimidazol-2-yl)methanol-κN,O)-bis(isothiocyanato-κN)nickel(II), C18H16N6NiO2S2
  33. Crystal structure of bis(2-(2′-hydroxy-5′-methoxyphenyl)-1H-benzimidazole)boron – tetrahydrofuran (1/1), C36H37N4O6B
  34. Crystal structure of poly[aqua-bis(nitrato-κ2O,O′)-(μ3-1,3-benzimidazol-3-ium-1,3-diacetato-κ4O,O′:O′′:O′′′)dysprosium(III)], C11H11DyN4O11
  35. Crystal structure of n-butyl-tris(dicyclo-hexylamido)hafnium(IV), C40H75HfN3
  36. Crystal structure of (E)-1-[1-(3-chloro-4-fluoro-phenyl)ethylidene]-2-(2,4-dinitrophenyl)hydrazine, C28H20Cl2F2N8O8
  37. The crystal structure of ethyl 4-((2-hydroxybenzyl)amino)benzoate, a Schiff base, C16H17NO3
  38. Crystal structure of 3-(2-(4-isobutylphenyl)propanoyl)-1-methylimidazolidine-2,4-dione, C17H22N2O3
  39. Crystal structure of poly[(μ3-2-(pyrazin-2-ylthio)acetato-κ3N:O:S)silver(I)], C6H5AgN2O2S
  40. Crystal structure of (E)-1-(3-((E)-((2-hydroxynaphthalen-1-yl)methylene)amino)phenyl)ethanone O-benzyl oxime, C26H22N2O2
  41. Crystal structure of (E)-2,3-dihydroxybenzaldehyde O-(2-((((E)-1-(2,5-dihydroxyphenyl)ethylidene)amino)oxy)ethyl) oxime monohydrate, C17H20N2O7
  42. Crystal structure of 4-(chloromethyl)-3-nitrobenzoic acid, C8H6ClNO4
  43. Crystal stucture of 4-((10H-phenothiazin-10-yl)methyl)-2,6-di-tert-butylphenol, C27H31NOS
  44. The crystal structure of ethyl 1-(4-nitrophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C13H10F3N3O4
  45. Crystal structure of catena-poly[di-(μ3-oxido-κ3O:O:O)-tetraoxido-(μ2-5′-(pyrazin-2-yl)-1H,2′H-3,3′-bi(1,2,4-triazole)-κ2N:N′)dimolybdenum(VI)], C8H6Mo2N8O6
  46. Crystal structure of (3,6-dioxocyclohexa-1,4-diene-1,4-bis(olato)-κ4O,O′:O′′,O′′′)-bis(tris(2-pyridylmethyl)amine-κ4N,N′,N′′,N′′′))-dizinc(II) bis(hexafluorophosphate(V)), C42H38F12N8O4P2Zn2
  47. Crystal structure of catena-poly[hexakis(μ2-2-acetylphenolato-κ3O:O,O′)trimanganese(II)], C48H42Mn3O12
  48. The crystal structure of 2,2-difluoro-4-(trifluoromethyl)-2,5-dihydro-[1,3,2]dioxaborinino[5,4-c]chromen-3-ium-2-uide, C11H6BF5O3
  49. Crystal structure of methyl (E)-2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazine-1-carboxylate, C13H19N3O3
  50. The crystal structure of tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate, C10H15N3O2
  51. Crystal structure of 1,1-bis(η5-adamantylcyclopentadienyl)-3-phenyl-2-trimethylsilyl-2,3-dihydroisotitanazole, C42H55NSiTi
  52. Crystal structure of 2-(4-(2-(4-benzylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C28H29N3O2
  53. Important impurity of Flupirtine – a single crystal study on ethyl (6-amino-5-((ethoxycarbonyl)amino)pyridin-2-yl)(4-fluorobenzyl)carbamate, C18H21FN4O4
  54. Crystal structure of ethyl 3-(4-methoxyphenyl)-1-(2-(4-methoxyphenyl)-2-oxoethyl)-1H-pyrazole-5-carboxylate, C22H22N2O5
  55. Crystal structure of 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate methanol solvate, C37H35N1O10
  56. The crystal structure of the inner salt of 2-[(aminoiminomethyl)amino]ethylcarbamic acid [systematic name: (2-((diaminomethylene)ammonio)ethyl)carbamate], C4H10N4O2
  57. Crystal structure of (8-hydroxy-5-nitroquinolinium) perchlorate – 8-hydroxy-5-nitroquinoline (1/1), C18H13ClN4O10
  58. The crystal structure of (5-methyl-1,2,4-oxadiazol-3-yl)ferrocene, C13H12FeN2O
  59. Crystal structure of methyl 1-(2-(fluorosulfonyl)ethyl)-2-oxocyclopentanecarboxylate, C9H13FO5S
  60. Crystal structure of the triclinic modification of 1-methyl-4-nitroimidzole, C4H5N3O2
  61. Corrigendum
  62. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
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