Startseite Synthesis and crystal structure of 5-(8-(((2-carboxyethyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate trihydrate, C19H23NO12S
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Synthesis and crystal structure of 5-(8-(((2-carboxyethyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate trihydrate, C19H23NO12S

  • Hai-Lin Chen und Xiu-Ju Yin EMAIL logo
Veröffentlicht/Copyright: 7. Dezember 2018
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 234 Heft 2

Abstract

C19H23NO12S, triclinic, P1̄ (no. 2), a = 8.3926(9) Å, b = 9.0469(6) Å, c = 15.3442(15) Å, α = 78.195(7)°, β = 74.352(9)°, γ = 70.169(8)°, V = 1047.08(18) Å3, Z = 2, Rgt(F) = 0.0538, wRref(F2) = 0.1289, T = 293(2) K.

CCDC no.: 1875398

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:Colorless block
Size:0.24 × 0.20 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.5 mm−1
Diffractometer, scan mode:Bruker SMART, φ and ω-scans
θmax, completeness:25°, >99%
N(hkl)measured, N(hkl)unique, Rint:7313, 3665, 0.040
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2399
N(param)refined:298
Programs:Bruker programs [1], SHELX [2, 3]
Table 2:

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

AtomxyzUiso*/Ueq
N10.1652(3)0.2549(3)0.63368(15)0.0360(6)
H1A0.2751700.2019540.6580440.054*
H1B0.1448700.3682540.6281440.054*
O1−0.2068(3)0.4878(3)0.72199(14)0.0566(7)
H1−0.2887270.5733230.7309650.085*
O20.0467(3)0.2301(3)1.09163(15)0.0601(8)
O30.1771(3)0.0475(2)0.85275(13)0.0414(6)
O40.6291(3)−0.3417(2)1.26093(13)0.0398(6)
H130.701981−0.4282341.2445760.060*
O50.5232(3)−0.0285(2)1.33179(14)0.0422(6)
O70.3207(3)−0.1802(2)1.39644(14)0.0488(6)
O60.2214(3)0.0909(2)1.32889(14)0.0491(7)
O80.1849(3)0.5319(3)0.51596(16)0.0600(7)
O90.4292(3)0.4971(2)0.40956(15)0.0511(6)
H9A0.4118380.5964260.4037380.077*
O100.5012(3)0.7197(2)0.77250(14)0.0547(7)
H10A0.4210560.6820490.7726260.082*
H10B0.4898660.8109490.7420160.082*
O110.7902(3)0.3579(2)0.23602(16)0.0604(8)
H11A0.8829340.3341630.1952330.091*
H11B0.8140340.3055730.2860230.091*
O120.8613(3)0.1729(3)0.39217(16)0.0712(8)
H12A0.9707690.1479920.3851950.107*
H12B0.8347690.2337430.4327250.107*
S10.36284(11)−0.05436(9)1.32767(5)0.0366(3)
C1−0.1380(4)0.4145(4)0.7949(2)0.0396(8)
C2−0.1838(4)0.4855(4)0.8745(2)0.0483(9)
H2−0.2649610.5852190.8786280.058*
C3−0.1090(4)0.4076(4)0.9460(2)0.0442(9)
H3−0.1400020.4555580.9987680.053*
C40.0131(4)0.2577(3)0.94238(19)0.0331(7)
C50.0565(4)0.1921(3)0.8619(2)0.0333(7)
C6−0.0188(4)0.2666(3)0.78747(19)0.0340(7)
C70.0929(4)0.1729(3)1.0191(2)0.0371(8)
C80.2261(4)0.0219(3)1.00335(19)0.0320(7)
C90.2563(4)−0.0275(4)0.9222(2)0.0412(8)
H90.341153−0.1240120.9126990.049*
C100.3275(4)−0.0765(3)1.07268(19)0.0325(7)
C110.3053(4)−0.0288(3)1.15695(19)0.0331(7)
H110.2230410.0668301.1713060.040*
C120.4024(4)−0.1198(3)1.22034(19)0.0323(7)
C130.5295(4)−0.2610(3)1.1997(2)0.0334(7)
C140.5482(4)−0.3119(4)1.1179(2)0.0419(8)
H140.628400−0.4090001.1044340.050*
C150.4514(4)−0.2227(4)1.0559(2)0.0435(9)
H150.468445−0.2603881.0009990.052*
C160.0291(4)0.1941(3)0.7008(2)0.0380(8)
H16A0.0723430.0797800.7134930.046*
H16B−0.0727210.2204700.6755270.046*
C170.2037(4)0.2102(3)0.5401(2)0.0416(8)
H17A0.1005470.2552630.5149390.050*
H17B0.2369510.0958830.5430560.050*
C180.3483(4)0.2698(3)0.4792(2)0.0443(9)
H18A0.3715140.2389500.4189800.053*
H18B0.4524330.2190800.5030640.053*
C190.3100(4)0.4464(4)0.4705(2)0.0397(8)

Source of material

The title compound was synthesized via a Mannich reaction. Formaldehyde solution (10 mL, 37%) and sodium 2-hydroxy-5-(7-hydroxy-4-oxo-4H-chromen-3-yl)benzenesulfonate (3.56 g, 0.01 mol) were added to ethanol (200 mL, 95%) and stirred for 0.5 h at 328 K. Then, the saturated solution of 3-aminopropionic acid (0.89 g, 0.01 mol) was added to the mixture. Hot water was added until a transparent solution was obtained. After 10 h reaction time, the mixture was filtered. The residue was dried at 383 K. Sodium 5-(8-(((2-carboxyethyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate (2.301 g) was obtained. This sodium salt (0.06 g) was added to a mixed solvent (methanol : tetrahydrofurane = 1 : 1, v/v) (60 mL) and sonicated for 10 min. After filtration, a transparent solution was obtained. After 3 days, colorless block crystals of the title compound were obtained.

Experimental details

H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 Ueq(C). According to Table 2 they are unrefined.

Discussion

Sodium 2-hydroxy-5-(7-hydroxy-4-oxo-4H-chromen-3-yl)benzenesulfonate (DSS) is a strongly water-soluble substance, produced by modifying the structure of daidzein [4]. Some studies have shown that DSS possessed excellent biological activities [5], [6], [7]. The Mannich reaction has been considered as an effective method in introducing aminomethyl substituents into the desired flavonoide molecules to improve their biological activities [8], [9], [10], [11], [12], [13], [14]. Our previous investigations showed that DSS can react with glycine, L-proline, L-Threonine by Mannich reaction [15], [16], [17]. The reaction takes place without a catalyst. When the sulfo-groups and carboxyl groups are introduced to daidzein, they can coordinate with some metal ions directly in intriguing ways. In this paper, we report a 3-aminopropanoic acid derivative of DSS.

The title compound contains one zwitterion and three water molecules in the asymmetric unit (cf. the figure). The bond distances and bond angles are in normal ranges [15], [16], [17]. The atoms of the chromen moiety constitute planar rings A (C1—C6) and C (C7—C9/O3/C5/C4) [mean out-of plane deviations are 0.0056 and 0.0144 Å, respectively], with an interplanar angle of 1.9°. There are π ⋯ π stacking interactions between C1—C6 phenyl rings and C10—C15 phenyl rings from adjacent compounds. The centroid-centroid distance is 3.8656(3) Å and the dihedral angle between the two phenyl least square planes is 4.25°. The C19—C18—C17—N1 torsion angle is −58.84°. The compounds shows an intramolecular N1—H1B⋯O8 hydrogen bond of length 2.062 Å. There exist various O—H⋯O and N—H⋯O hydrogen bonds. In the crystal the ylidic title compound and water molecules interact via hydrogen bonds. Together with the π⋯π stacking interactions a three-dimensional network is obtained.

Acknowledgements

This work was supported by the project of education department of Guangxi province (No. YB2014331), the project of undergraduate teaching reform of higher education in Guangxi (No. 2018JGA254) and the subject of “12th Five-Year” Plan of Guangxi Education Science (No. 2015C408).

References

1. Bruker. APEX3, SAINT-Plus, XPREP. Bruker AXS Inc., Madison, WI, USA (2016).Suche in Google Scholar

2. Sheldrick, G. M.: SHELXT − Integrated space-group and crystal-structure determination. Acta Crystallogr. A71 (2015) 3–8.10.1107/S2053273314026370Suche in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

4. Chen, H.-L.; Miao, J.-H.; Lin, F.-Q.; Pan, W.-G.; Lin, C.-W.: Crystal structure of dipotassium 2-(2-ethoxy-2-oxoethoxy)-5-(7-(2-ethoxy-2-oxoethoxy)-4-oxo-4H-chromen-3-yl)benzenesulfonate), C23H21KO11S. Z. Kristallogr. NCS 229 (2014) 476–478.10.1515/ncrs-2014-0127Suche in Google Scholar

5. Liu, R.; Zhong, X.; Zeng, J.; Huang, Z.; Li, X.; Xiao, H.; Chen, Q.; Li, D.: 3′-daidzein sulfonate sodium inhibits neuronal apoptosis induced by cerebral ischemia-reperfusion. Int. J. Mol. Med. 39 (2017) 1021–1028.10.3892/ijmm.2017.2915Suche in Google Scholar PubMed

6. Ren, P.; Ji, H.; Shao, Q.; Chen, X.; Han, J.; Sun, Y.: Protective effects of sodium daidzein sulfonate on trabecular bone in ovariectomized rats. Pharmacology 79 (2007) 129–136.10.1159/000098115Suche in Google Scholar PubMed

7. Huang, Z.; Li, L.; Li, X.; Cheng, F.; Zeng, J.: Effect of 3′-daidzein sulfonic sodium on the anti-oxidation of retinal ischemia/reperfusion injury in rats. Adv. Exp. Med. Biol. 664 (2010) 585–591.10.1007/978-1-4419-1399-9_67Suche in Google Scholar PubMed

8. Aitmambetov, A.; Khilya, V. P.: Mannich bases and their salts in a series of synthetic isoflavone analogs. Chem. Nat. Compd. 30 (1994) 576–579.10.1007/BF00629866Suche in Google Scholar

9. Frasinyuk, M. S.; Bondarenko, S. P.; Khilya, V. P.: Synthesis of analogs of natural 2′-methoxyisoflavones. Chem. Nat. Compd. 42 (2006) 142–147.10.1007/s10600-006-0063-0Suche in Google Scholar

10. Frasinyuk, M. S.; Mrug, G. P.; Fedoryak, O. D.; Bondarenko, S. P.: Nitrogen-containing apigenin analogs: preparation and biological activity. Molecules 17 (2012) 14748–14764.10.3390/molecules171214748Suche in Google Scholar PubMed PubMed Central

11. Frasinyuk, M. S.; Mrug, G. P.; Fedoryak, O. D.; Bondarenko, S. P.: Synthesis of amino-acid derivatives of formononetin and cladrin. Chem. Nat. Compd. 48 (2012) 570–573.10.1007/s10600-012-0313-2Suche in Google Scholar

12. Frasinyuk, M. S.; Mrug, G. P.; Bondarenko, S. P.; Sviripa, V. M.; Zhang, W.; Cai, X.; Fiandalo, M. V.; Mohler, J. L.; Liu, C.; Watt, D. S.: Application of Mannich bases to the synthesis of hydroxy-methylated isoflavonoids as potential antineoplastic agents. Org. Biomol. Chem. 13 (2015) 11292–11301.10.1039/C5OB01828ESuche in Google Scholar

13. Frasinyuk, M. S.; Mrug, G. P.; Bondarenko, S. P.; Khilya, V. P.; Sviripa, V. M.; Syrotchuk, O. A.; Zhang, W.; Cai, X.; Fiandalo, M. V.; Mohler, J. L.: Antineoplastic Isoflavonoids Derived from Intermediate ortho-Quinone Methides Generated from Mannich Bases. Chem. Med. Chem. 11 (2016) 600–611.10.1002/cmdc.201600008Suche in Google Scholar PubMed PubMed Central

14. Li, Y.; Qiang, X.; Luo, L.; Yang, X.; Xiao, G.; Zheng, Y.; Cao, Z.; Sang, Z.; Su, F.; Deng, Y.: Multitarget drug design strategy against Alzheimers disease: homoisoflavonoid Mannich base derivatives serve as acetylcholinesterase and monoamine oxidase B dual inhibitors with multifunctional properties. Bioorg. Med. Chem. 25 (2017) 714–726.10.1016/j.bmc.2016.11.048Suche in Google Scholar PubMed

15. Chen, H.-L.; Lai, H.-F.; Qin, Y.-L.; Guo, Y.-N.; Chen, T.; Huang, X.-Y.: Synthesis and crystal structure poly[aqua(μ3-2-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)acetate-κ4O,O′: O′′:O′′′) sodium] monohydrate, C18H18NNaO11S. Z. Kristallogr. NCS 233 (2018) 417–419.10.1515/ncrs-2017-0321Suche in Google Scholar

16. Chen, H.-L.; Pan, L.-W.; Zhang, H.-Y.; Yin, X.-J.: Synthesis and crystal structure of poly[aqua{μ3-(1S,2S)-1-((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo- 4H-chromen-8-yl)methyl)pyrrolidin-1-ium-2-carboxylato-κ4O, O′:O′′: O′′′}sodium(I)] monohydrate, C21H22NNaO11S. Z. Kristallogr. NCS 233 (2018) 469–471.10.1515/ncrs-2017-0360Suche in Google Scholar

17. Chen, H.-L.; Lai, H.-F.; Wei, L.-Q.; Jiang, L.-R.; Su, Y.-X.: 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. Z. Kristallogr. NCS 232 (2017) 1025–1027.10.1515/ncrs-2017-0153Suche in Google Scholar

Received: 2018-08-14
Accepted: 2018-10-25
Published Online: 2018-12-07
Published in Print: 2019-03-26

©2019 Hai-Lin Chen et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of 1H-indole-5-carboxylic acid – 4,4′-bipyridine (2/1), C14H11N2O2
  3. Crystal structure of ethyl 2-amino-4-(4-ethoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO6
  4. Crystal structure of ethyl 2-amino-4-(4-bromothiophen-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C16H16BrNO4S
  5. The crystal structure of 6-amino-2-methyl-8-(4-(methylthio)phenyl)-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile – ethanol (1/1), C20H19N5S
  6. Crystal structure of 6-amino-8-(4-isopropylphenyl)-2-methyl-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile-ethanol (1/1), C24H29N5O
  7. Crystal structure of 1,1′-(ethane-1,2-diyl)bis(3-ethyl-1H-imidazol-3-ium)bis(hexafluorido phosphate), C12H20F12N4P2
  8. Crystal structure of dimethyl (3aS,6R,6aS,7S)-2-pivaloyl-2,3-dihydro-1H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isoquinoline-3a1,6a-dicarboxylate, C21H25NO8
  9. Crystal structure of methyl 4-(4-bromothiophen-2-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H20BrNO3S
  10. Hydrothermal synthesis and crystal structure of catena-poly[bis(4-((pyridin-4-ylmethyl)amino)benzoato-κ3N:O,O′)zinc(II) – 1,2-di(pyridin-4-yl)ethene – water (1/1/1), C38H34N6O5Zn
  11. The crystal structure of 1,2-dimethyl-3,4-dinitrobenzene, C8H8N2O4
  12. Synthesis and crystal structure of trans-tetraaqua-bis(3-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)propanoato-κO)zinc(II) tetrahydrate, C38H48N2O26S2Zn
  13. Crystal structure of diaqua-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-tetrakis(chloropyridin-2-olato-κ1O)-bis(penanthroline-κ2N,N′)diterbium(III), C54H38Cl6Tb2N10O8
  14. Crystal structure of oxidobis(piperidine-1-carbodithioato-κ2S,S′)vanadium(IV), C12H20N2OS4V
  15. Crystal structure of 2-((tert-butyldimethylsilyl)oxy)-5-methylisophthalaldehyde, C15H22O3Si
  16. Crystal structure of catena-poly[tetraiodido-(μ2-1,4-bis(2-methyl-1H-imidazol-1-yl)benzene-κ2N:N′)dimercury(II)], C14H14Hg2I4N4
  17. Crystal structure of tetrakis(n-butyl)-(μ2-1,2-bis(2-oxidobenzoyl)hydrazine-1,2-diido-κ6N,O,O′:N′,O′′,O′′′)ditin(IV), C30H44N2O4Sn2
  18. Crystal structure of ethyl 2-amino-4-(4-hydroxy-3-methoxyphenyl)-7-methyl-5-oxo-4H,5H-pyrano-[4,3-b]pyran-3-carboxylate, C19H19NO7
  19. Crystal structure of 3-aminopyrazine-2-carbohydrazide, C5H7N5O
  20. Crystal structure of ethanol-bis(N-((5-(ethoxycarbonyl)-3,4-dimethyl-1H-pyrrol-2-yl)methylene)benzohydrazonato-κ2N,O)copper(II), C36H42N6O7Cu
  21. Crystal structure of 3-methyl-2-oxo-2H-chromen-7-yl propionate, C13H12O4
  22. Crystal structure of 2-(dimethylamino)ethyl 4-aminobenzoate, C11H16N2O2
  23. Crystal structure of 3-(benzo[d]thiazol-2-ylamino)isobenzofuran-1(3H)-one, C15H10N2O2S
  24. Crystal structure of 3-((1H-benzo[d]imidazol-2-yl)amino)-2-(1H-benzo[d]imidazol-2-yl)isoindolin-1-one, C22H16N6O
  25. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(4-(dimethylamino)phenyldiphenylphosphane-κP)copper(I) tetrafluoroborate, C50H48BCuF4N4P2
  26. Crystal structure of citric acid–acetonitrile (1/1), C8H11NO7
  27. Crystal structure of diethyl 2-(4-methoxyphenyl)-1-phenyl-1,2-dihydropyridine-3,5-dicarboxylate, C24H25NO5
  28. The crystal structure of poly[triaqua-bis(μ3-2,5-dihydroxyterephthalato-κ4O,O′:O′′:O′′′)-(μ4-oxalato-κ4O,O′:O′′,O′′′)cerium(III)], C9H10CeO11
  29. Crystal structure of 1-(5-(anthracen-9-yl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O2
  30. Synthesis and crystal structure of 5-(8-(((2-carboxyethyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate trihydrate, C19H23NO12S
  31. Crystal structure of rac-trans-6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromophenolato-κ4N,N′,O,O′)-bis(methanol)cobalt(III) chloride, C22H25Br2Co8N2O4Cl
  32. Crystal structure of 1-((R)-(2′-(dimethylamino)-[1,1′-binaphthalen]-2-yl))-3-((S)-2-hydroxy-1-phenylethyl)thiourea, C31H29N3OS
  33. Crystal structure and photochemical property of 1,8-bis(p-tolylthio)pyrene, C30H22S2
  34. Crystal structure of 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate, C14H18ClN5O4
  35. Crystal structure of ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate, C11H12N4O2
  36. Crystal structure of trichloro-(4-chloro-2,6-bis(diphenylmethyl)-N-((pyridin-2-yl)methylene)aniline)-aluminum dichloromethane solvate, C39H31AlCl6N2
  37. Bis(ethanol-κO)-bis(6-aminopicolinato-κ2N,O)magnesium(II), C16H22O6N4Mg
  38. Crystal structure of catena-poly[aqua-(μ2-1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ2O:O′)-(1,10-phenanthrolin-κ2N,N′)copper(II)], C16H20B10CuN2O5
  39. Crystal structure of (1,2-dicarba-closo-dodecaborane-1,2-dithiolato κ2S,S′)-bis(1,10-phenanthroline κ2N,N′)zinc(II), C26H26B10Zn4S2
  40. Crystal structure of diaqua-bis(1,10-phenanthroline-κ2N,N′)-bis(1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ3O,O′:O′′) dicobalt(II) — ethanol (1/1), C34H46B20Co2N4O11
  41. Crystal structure of ((5,5′-dimethoxy-2,2′-(1,2-phenylenebis(nitrilomethylidyne)))diphenolato-κ4O,N,O′,N′)copper(II), C22H18N2CuO4
  42. Crystal structure of 1-(5-bromo-2-(4-methoxyphenyl)-1H-indol-7-yl)ethan-1-ol, C17H14BrNO2
  43. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, C34H34N5O2Br
  44. Crystal structure of (Z)-2-((adamantan-1-ylimino)methyl)-5-methoxyphenol, C18H23NO2
  45. Crystal structure of bis((E)-2-ethoxy-6-(((2-hydroxyethyl)imino)methyl)phenolato-κ2N,O)copper(II), C22H28N2CuO6
  46. Crystal structure of 2,3-diphenyl-5,6-bis(4-methoxyphenyl)pyrazine, C30H24N2O2
  47. Crystal structure of dichlorido bis[1-((2,4-dimethyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN]cadmium(II), Cd(C12H13N5)2Cl2
  48. The crystal structure of 1,5-di(naphthalen-2-yl)-3-(pyridin-2-yl)pentane-1,5-dione, C30H23NO2
  49. The crystal structure of 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S
  50. The crystal structure of 1,4-dinitroso-2,3,5,6-tetraacetoxy-piperazine, C12H16N4O10
  51. Crystal structure of bis(2,4,6-trichlorophenyl) malonate, C15H6Cl6O4
  52. The crystal structure of trans-dichlorido-bis(pyridine-2-carboxylato-κ2N,O)platinum(IV), C12H8Cl2N2O4Pt
  53. Crystal structure of 3-nitroquinoline 1-oxide, C9H6N2O3
  54. Crystal structure of 2-(piperidin-1-ium-4-yl)-1H-benzo[d]imidazol-3-ium dichloride dihydrate, C12H21Cl2N3O2
  55. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene, C30H50O
  56. Crystal structure of (E)-4-((2-fluoro-3-(trifluoromethyl)benzylidene)amino)-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C11H8F4N4S
  57. Crystal structure of 5-(4-fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C9H8FN3S
  58. Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n
  59. The crystal structure of 4-(methoxycarbonyl)benzoic acid, C9H8O4
  60. The crystal structure of N,N′-(6-(thiophen-2-yl)-1,3,5-triazine-2,4-diyl)bis(2-methylpropane-2-sulfonamide) – ethyl acetate(2/1), C34H54N10O6S6
  61. Crystal structure of N′-(1-(2-hydroxyphenyl)ethylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide, C18H17N5O2
  62. Crystal structure of 3-(4-methoxyphenyl)-1-phenylprop-2-yn-1-one, C16H12O2
  63. Crystal structure of N′-(1-(benzofuran-2-yl)ethylidene)-2-cyanoacetohydrazide, C13H11N3O2
  64. Crystal structure of hexa-μ2-chlorido-μ4-oxido-tetrakis(1-vinyl-1H-imidazole-κN)tetracopper(II), C20H24Cu4Cl6N8O
  65. Crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide, C22H22O5N2S
  66. Crystal structure of 2-acetyl pyrene, C18H12O
https://doi.org/10.1515/ncrs-2018-0307
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Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of 1H-indole-5-carboxylic acid – 4,4′-bipyridine (2/1), C14H11N2O2
  3. Crystal structure of ethyl 2-amino-4-(4-ethoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO6
  4. Crystal structure of ethyl 2-amino-4-(4-bromothiophen-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C16H16BrNO4S
  5. The crystal structure of 6-amino-2-methyl-8-(4-(methylthio)phenyl)-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile – ethanol (1/1), C20H19N5S
  6. Crystal structure of 6-amino-8-(4-isopropylphenyl)-2-methyl-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile-ethanol (1/1), C24H29N5O
  7. Crystal structure of 1,1′-(ethane-1,2-diyl)bis(3-ethyl-1H-imidazol-3-ium)bis(hexafluorido phosphate), C12H20F12N4P2
  8. Crystal structure of dimethyl (3aS,6R,6aS,7S)-2-pivaloyl-2,3-dihydro-1H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isoquinoline-3a1,6a-dicarboxylate, C21H25NO8
  9. Crystal structure of methyl 4-(4-bromothiophen-2-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H20BrNO3S
  10. Hydrothermal synthesis and crystal structure of catena-poly[bis(4-((pyridin-4-ylmethyl)amino)benzoato-κ3N:O,O′)zinc(II) – 1,2-di(pyridin-4-yl)ethene – water (1/1/1), C38H34N6O5Zn
  11. The crystal structure of 1,2-dimethyl-3,4-dinitrobenzene, C8H8N2O4
  12. Synthesis and crystal structure of trans-tetraaqua-bis(3-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)propanoato-κO)zinc(II) tetrahydrate, C38H48N2O26S2Zn
  13. Crystal structure of diaqua-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-tetrakis(chloropyridin-2-olato-κ1O)-bis(penanthroline-κ2N,N′)diterbium(III), C54H38Cl6Tb2N10O8
  14. Crystal structure of oxidobis(piperidine-1-carbodithioato-κ2S,S′)vanadium(IV), C12H20N2OS4V
  15. Crystal structure of 2-((tert-butyldimethylsilyl)oxy)-5-methylisophthalaldehyde, C15H22O3Si
  16. Crystal structure of catena-poly[tetraiodido-(μ2-1,4-bis(2-methyl-1H-imidazol-1-yl)benzene-κ2N:N′)dimercury(II)], C14H14Hg2I4N4
  17. Crystal structure of tetrakis(n-butyl)-(μ2-1,2-bis(2-oxidobenzoyl)hydrazine-1,2-diido-κ6N,O,O′:N′,O′′,O′′′)ditin(IV), C30H44N2O4Sn2
  18. Crystal structure of ethyl 2-amino-4-(4-hydroxy-3-methoxyphenyl)-7-methyl-5-oxo-4H,5H-pyrano-[4,3-b]pyran-3-carboxylate, C19H19NO7
  19. Crystal structure of 3-aminopyrazine-2-carbohydrazide, C5H7N5O
  20. Crystal structure of ethanol-bis(N-((5-(ethoxycarbonyl)-3,4-dimethyl-1H-pyrrol-2-yl)methylene)benzohydrazonato-κ2N,O)copper(II), C36H42N6O7Cu
  21. Crystal structure of 3-methyl-2-oxo-2H-chromen-7-yl propionate, C13H12O4
  22. Crystal structure of 2-(dimethylamino)ethyl 4-aminobenzoate, C11H16N2O2
  23. Crystal structure of 3-(benzo[d]thiazol-2-ylamino)isobenzofuran-1(3H)-one, C15H10N2O2S
  24. Crystal structure of 3-((1H-benzo[d]imidazol-2-yl)amino)-2-(1H-benzo[d]imidazol-2-yl)isoindolin-1-one, C22H16N6O
  25. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(4-(dimethylamino)phenyldiphenylphosphane-κP)copper(I) tetrafluoroborate, C50H48BCuF4N4P2
  26. Crystal structure of citric acid–acetonitrile (1/1), C8H11NO7
  27. Crystal structure of diethyl 2-(4-methoxyphenyl)-1-phenyl-1,2-dihydropyridine-3,5-dicarboxylate, C24H25NO5
  28. The crystal structure of poly[triaqua-bis(μ3-2,5-dihydroxyterephthalato-κ4O,O′:O′′:O′′′)-(μ4-oxalato-κ4O,O′:O′′,O′′′)cerium(III)], C9H10CeO11
  29. Crystal structure of 1-(5-(anthracen-9-yl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O2
  30. Synthesis and crystal structure of 5-(8-(((2-carboxyethyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate trihydrate, C19H23NO12S
  31. Crystal structure of rac-trans-6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromophenolato-κ4N,N′,O,O′)-bis(methanol)cobalt(III) chloride, C22H25Br2Co8N2O4Cl
  32. Crystal structure of 1-((R)-(2′-(dimethylamino)-[1,1′-binaphthalen]-2-yl))-3-((S)-2-hydroxy-1-phenylethyl)thiourea, C31H29N3OS
  33. Crystal structure and photochemical property of 1,8-bis(p-tolylthio)pyrene, C30H22S2
  34. Crystal structure of 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate, C14H18ClN5O4
  35. Crystal structure of ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate, C11H12N4O2
  36. Crystal structure of trichloro-(4-chloro-2,6-bis(diphenylmethyl)-N-((pyridin-2-yl)methylene)aniline)-aluminum dichloromethane solvate, C39H31AlCl6N2
  37. Bis(ethanol-κO)-bis(6-aminopicolinato-κ2N,O)magnesium(II), C16H22O6N4Mg
  38. Crystal structure of catena-poly[aqua-(μ2-1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ2O:O′)-(1,10-phenanthrolin-κ2N,N′)copper(II)], C16H20B10CuN2O5
  39. Crystal structure of (1,2-dicarba-closo-dodecaborane-1,2-dithiolato κ2S,S′)-bis(1,10-phenanthroline κ2N,N′)zinc(II), C26H26B10Zn4S2
  40. Crystal structure of diaqua-bis(1,10-phenanthroline-κ2N,N′)-bis(1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ3O,O′:O′′) dicobalt(II) — ethanol (1/1), C34H46B20Co2N4O11
  41. Crystal structure of ((5,5′-dimethoxy-2,2′-(1,2-phenylenebis(nitrilomethylidyne)))diphenolato-κ4O,N,O′,N′)copper(II), C22H18N2CuO4
  42. Crystal structure of 1-(5-bromo-2-(4-methoxyphenyl)-1H-indol-7-yl)ethan-1-ol, C17H14BrNO2
  43. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, C34H34N5O2Br
  44. Crystal structure of (Z)-2-((adamantan-1-ylimino)methyl)-5-methoxyphenol, C18H23NO2
  45. Crystal structure of bis((E)-2-ethoxy-6-(((2-hydroxyethyl)imino)methyl)phenolato-κ2N,O)copper(II), C22H28N2CuO6
  46. Crystal structure of 2,3-diphenyl-5,6-bis(4-methoxyphenyl)pyrazine, C30H24N2O2
  47. Crystal structure of dichlorido bis[1-((2,4-dimethyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN]cadmium(II), Cd(C12H13N5)2Cl2
  48. The crystal structure of 1,5-di(naphthalen-2-yl)-3-(pyridin-2-yl)pentane-1,5-dione, C30H23NO2
  49. The crystal structure of 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S
  50. The crystal structure of 1,4-dinitroso-2,3,5,6-tetraacetoxy-piperazine, C12H16N4O10
  51. Crystal structure of bis(2,4,6-trichlorophenyl) malonate, C15H6Cl6O4
  52. The crystal structure of trans-dichlorido-bis(pyridine-2-carboxylato-κ2N,O)platinum(IV), C12H8Cl2N2O4Pt
  53. Crystal structure of 3-nitroquinoline 1-oxide, C9H6N2O3
  54. Crystal structure of 2-(piperidin-1-ium-4-yl)-1H-benzo[d]imidazol-3-ium dichloride dihydrate, C12H21Cl2N3O2
  55. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene, C30H50O
  56. Crystal structure of (E)-4-((2-fluoro-3-(trifluoromethyl)benzylidene)amino)-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C11H8F4N4S
  57. Crystal structure of 5-(4-fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C9H8FN3S
  58. Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n
  59. The crystal structure of 4-(methoxycarbonyl)benzoic acid, C9H8O4
  60. The crystal structure of N,N′-(6-(thiophen-2-yl)-1,3,5-triazine-2,4-diyl)bis(2-methylpropane-2-sulfonamide) – ethyl acetate(2/1), C34H54N10O6S6
  61. Crystal structure of N′-(1-(2-hydroxyphenyl)ethylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide, C18H17N5O2
  62. Crystal structure of 3-(4-methoxyphenyl)-1-phenylprop-2-yn-1-one, C16H12O2
  63. Crystal structure of N′-(1-(benzofuran-2-yl)ethylidene)-2-cyanoacetohydrazide, C13H11N3O2
  64. Crystal structure of hexa-μ2-chlorido-μ4-oxido-tetrakis(1-vinyl-1H-imidazole-κN)tetracopper(II), C20H24Cu4Cl6N8O
  65. Crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide, C22H22O5N2S
  66. Crystal structure of 2-acetyl pyrene, C18H12O
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Heruntergeladen am 18.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2018-0307/html
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