Startseite Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one, C15H14O2S
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Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one, C15H14O2S

  • Ya-Xin Wen , Ya-Fei Guo ORCID logo EMAIL logo , Le Dong , Jun-Ying Ma und Bing-You Fan
Veröffentlicht/Copyright: 22. März 2022
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 237 Heft 3

Abstract

C15H14O2S, monoclinic, P21/c (no. 14), a = 13.5881(11) Å, b = 7.3129(9) Å, c = 13.3284(11) Å, β = 96.125(7)°, V = 1316.9(2) Å3, Z = 4, R gt (F) = 0.0570, wRref(F2) = 0.1402, T = 293 K.

CCDC no.: 2123340

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: Brown block
Size: 0.20 × 0.16 × 0.15 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.24 mm−1
Diffractometer, scan mode: SuperNova, ω
θmax, completeness: 28.3°, >99%
N(hkl)measured, N(hkl)unique, Rint: 5547, 2725, 0.022
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2014
N(param)refined: 169
Programs: CrysAlisPRO [1], Olex2 [2], SHELX [3]
Table 2:

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

Atom x y z Uiso*/Ueq
S1 0.14502 (5) 0.74734 (11) 0.61439 (5) 0.0502 (2)
O1 0.12386 (15) 0.2882 (3) 0.45978 (18) 0.0690 (6)
H1 0.102 (3) 0.400 (8) 0.376 (4) 0.17 (2)*
O2 0.07901 (15) 0.5401 (4) 0.34290 (13) 0.0642 (6)
C1 0.33959 (17) 0.7432 (4) 0.56455 (16) 0.0389 (6)
H1A 0.3176 0.6754 0.5075 0.047*
C2 0.27362 (17) 0.7959 (4) 0.62994 (16) 0.0389 (6)
C3 0.30661 (18) 0.8987 (4) 0.71634 (16) 0.0448 (7)
H3 0.2616 0.9345 0.7605 0.054*
C4 0.40301 (19) 0.9461 (4) 0.73587 (17) 0.0474 (7)
H4 0.4232 1.0146 0.7931 0.057*
C5 0.57510 (19) 0.9388 (4) 0.6891 (2) 0.0548 (8)
H5 0.5976 1.0050 0.7466 0.066*
C6 0.6399 (2) 0.8874 (5) 0.6241 (2) 0.0631 (9)
H6 0.7065 0.9176 0.6376 0.076*
C7 0.6073 (2) 0.7887 (5) 0.5366 (2) 0.0622 (9)
H7 0.6524 0.7553 0.4920 0.075*
C8 0.51042 (19) 0.7414 (4) 0.51634 (19) 0.0491 (7)
H8 0.4897 0.6760 0.4581 0.059*
C9 0.44101 (17) 0.7910 (4) 0.58321 (16) 0.0387 (6)
C10 0.47349 (17) 0.8931 (4) 0.67077 (16) 0.0410 (6)
C11 0.12970 (16) 0.5916 (4) 0.51345 (17) 0.0415 (6)
C12 0.14117 (17) 0.4027 (5) 0.5316 (2) 0.0524 (7)
C13 0.1742 (2) 0.3276 (6) 0.6336 (3) 0.0793 (10)
H13A 0.1764 0.1965 0.6302 0.119*
H13B 0.1284 0.3640 0.6800 0.119*
H13C 0.2389 0.3738 0.6562 0.119*
C14 0.09843 (17) 0.6553 (4) 0.41561 (18) 0.0478 (7)
C15 0.0846 (2) 0.8509 (5) 0.3894 (2) 0.0712 (9)
H15A 0.0690 0.8630 0.3178 0.107*
H15B 0.1444 0.9166 0.4104 0.107*
H15C 0.0314 0.8998 0.4231 0.107*

Source of material

To a solution of acetylacetone (0.200 g, 2 mmol) and 2-naphthalenethiol (0.160 g, 1 mmol) in DMSO (1 mL) was added Cs2CO3 (0.326 mg, 1 mmol). The mixture was stirred at 45 °C under oxygen atmosphere for 10 h. The mixture was then added to water (5 mL). The resulting mixture was extracted with ethylether (10 mL) for three times. The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. After removal of the solvent, the residue was then purified by flash column chromatography on silica gel with petroleum ether/ethyl acetate (45:1) to give the desired (245 mg, 95%) as a white solid. Single crystals suitable for X-ray diffraction were obtained by crystallization of the title compound from ethyl acetate. Melting point: 88–89 °C. 1 H NMR (400 MHz, CDCl3, 298 K) δ 17.47 (s, 1H), 7.84–7.78 (m, 2H), 7.76(d, J = 8.6 Hz, 1H), 7.53–7.43 (m, 3H), 7.32 (d, J = 8.6 Hz, 1H), 2.43 (s, 6H). 13 C NMR (101 MHz, CDCl3) δ 198.4, 135.3, 133.9, 131.4, 128.9, 127.8, 126.8, 125.4, 123.6, 121.8, 101.4, 24.4.

Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Comment

β-dicarbonyl thioether belong to an important class of compounds, which are of great demand in organic synthesis as well as in the pharmaceutical industry [4, 5]. From a synthetic perspective, these compounds have frequently used as valuable starting materials or reactive intermediates in a variety of organic transformations [6], [7], [8]. For example, they have been used as precursors for a large number of target molecules [9]. Besides, β-dicarbonyl thioether have applications in the pharmaceutical and agrochemical industries. Examples of β-dicarbonyl thioethers as pharmaceutical building blocks or intermediates include anti-inflammatory [10], anti-HSV-1 [11], and antimicrobial properties [12]. In this paper we report the synthesis and crystal structure of a β-dicarbonyl thioether.

The assymmetric unit contains one molecule of the title compound, which is constructed by the acetylacetone and the 2-naphthalenethiol (see the figure). The acetylacetone fragment together with the sulfur almost in a strict plane, whereby the largest deviation for the S1 atom from the acetylacetone plane is 0.137 Å. The dihedral angle between the acetylacetone group and 2-naphthalenethiol group is found to be 88.26°. The C(2)–S(1)–C(11)–C(14) and C(2)–S(1)–C(11)–C(12) torsion angles are −97.72(19)° and 87.20(2)°. The C(2)–S(1)–C(11) bond angle is 104.71(11)°. The thioether bond distances are 1.758(3) Å for C(11)–S(1) and 1.773(2) Å for C(2)–S(1), respectively, which are typical Caryl–S bond distances. The lengths of C(2)–C(1), C(2)–C(3) bond in benzene ring are 1.371(3) and 1.408(3) Å respectively. Within the acetylacetone unit, the dimensions and planarity are consistent with their adoption of a delocalized enol form. The bond lengths of C(11)–C(14), C(11)–C(12) are 1.407(3) Å and 1.409(4) Å respectively. In the crystal structure, the two oxygen atoms are linked by an intramolecular O(1)–H(1)⃛O(2) hydrogen bond. The distance of O(1)⃛H(1) is 1.400(5) Å and the distance of O(2)⃛H(1) is 1.140(6) Å. The structure of the molecule is similar to the stereo-configuration of the compound reported in the references [13], [14], [15]. The bond lengths and angles are all in the expected ranges. The complete set of X-ray diffraction data for the title compound was deposited to the Cambridge Crystallographic Data Centre (CCDC entry no. 2123340).

Corresponding author: Ya-Fei Guo, School of Chemical Engineering and Pharmaceutics, Henan University of Science and Technology, Luoyang, Henan 471003, P. R. China, E-mail:

Funding source: Programs for Science and Technology Development of Henan Province http://dx.doi.org/10.13039/501100011447

Award Identifier / Grant number: 212102210650

Funding source: Key Research Project for Colleges and Universities of Henan Province

Award Identifier / Grant number: 21B530002

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was supported by the Programs for Science and Technology Development of Henan Province, China (No. 212102210650) and the Key Research Project for Colleges and Universities of Henan Province, China (No. 21B530002).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2022-02-03
Accepted: 2022-03-03
Published Online: 2022-03-22
Published in Print: 2022-06-27

© 2022 Ya-Xin Wen et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-(4-imidazol-1-yl-phenyl)-(2-methoxy-benzylidene)-amine monohydrate, C17H17N3O2
  4. Crystal structure of 6-methyl-3-(pyrrolidine-1-carbonyl)-2H-chromen-2-one, C15H15N1O3
  5. Crystal structure of 4-methyl-4-nitropentanoic acid, C6H11NO4
  6. The crystal structure of (E)-3-(furan-2-yl)acrylonitrile, C7H5NO
  7. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)-1H-pyrazole-4-carboxamide monohydrate, C23H26F2N4O3
  8. Crystal structure of 2-(4-bromobenzyloxy)-6-chloropyridine, C12H9BrClNO
  9. Crystal structure of N-(4-bromo-2,6-dichloro-phenyl)pyrazin-2-amine, C10H6BrCl2N3
  10. Crystal structure of (E)-1-(2–nitrophenyl)-3-phenylprop-2-en-1-one, C15H11NO3
  11. The crystal structure of (E)-3-chloro-2-(2-(4-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  12. Crystal structure of (E)-amino(2-(thiazol-2-ylmethylene)hydrazineyl)methaniminium nitrate, C10H16N12O6S2
  13. Crystal structure of 9-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C15H18N4O
  14. The crystal structure bis(dimethylsulfoxide-κ1O)-dipyridine-κ1 N-bis(m2-(Z)-3-methyl-2-oxido-N-((Z)-oxido(phenyl)methylene)benzohydrazonato-κ5)trinickel(II) - dimethylsulfoxide (1/2), C48H56N6Ni3O10S4
  15. Crystal structure of bis(bis(triphenylphosphine)iminium) tetradecacarbonyltetratelluridopentaferrate(2-), (PPN)2[Fe5Te4(CO)14]
  16. Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one, C15H14O2S
  17. The crystal structure of [(1,10-phenanthroline-κ2 N,N)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)nickel(II)] monohydrate, C36H26N4O5Ni
  18. Crystal structure of 3,3′-(pyridine-2,6-diylbis(methylene))bis(1-propyl-1H-imidazol-3-ium) ditetrafluoroborate, C19H27B2F8N5
  19. The crystal structure of (E)-1-(4-aminophenyl)-3-(p-tolyl)prop-2-en-1-one, C16H15NO
  20. The crystal structure of poly[(μ2-terephthalato-κ4O,O′: O″,O‴)-(μ4-terephthalato-κ4O:O′:O″:O‴)-{μ4-(1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ4O:O′:O″,O‴)}dicadmium(II)] – water – acetronitrile (1/2/2), C38H36N14O10Cd2
  21. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)cobalt(II)–water–N,N-dimethylformamide(1/2/1), C27H31N3O9Co
  22. The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid – 4,4′-bipyridine, C8H8O4·C10H8N2
  23. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)cobalt(II)], C32H22Br2CoN4O4
  24. Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione – methanol (1/1), C11H13N5S
  25. The crystal structure of (Z)-4-bromo-6-(((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)methylene)cyclohexa-2,4-dien-1-one monohydrate, C11H16BrNO5
  26. Crystal structure of bis(tetrapropylammonium) nonaselenidotetrastannate(IV), (Pr4N)2[Sn4Se9]
  27. Crystal structure of 2,6-di-tert-butyl-4-(4-chlorobenzylidene)cyclohexa-2,5-dien-1-one, C21H25ClO
  28. Crystal structure of (2,2′-((naphthalen-1-ylmethyl)azanediyl)diacetato-κ3 N,O,O′)-(1,10-phenanthroline-κ2 N,N′)-copper(II) trihydrate, CuC27H27N3O7
  29. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylato-κ2N,O)-bis(1H-pyrazol-3-ylamine-κ2 N:N)dicobalt(II) dihydrate, C27H23N5O5Co
  30. The crystal structure of bis((E)-2-((tert-butylimino)methyl)-4-chlorophenolato-κ2N,O)zinc(II), C22H26Cl2N2O2Zn
  31. The crystal structure of poly[diaqua-(μ3-5-nitrobenzene-1,2,3-tricarboxylato-κ3O:O′:O′)-(μ2-4,4′-dipyridylamine-κ2N:N′)copper(II)], C38H30Cu3N8O20
  32. The crystal structure of (E)-1-ferrocenyl-3-(naphthalen-1-yl)prop-2-en-1-one, C23H18FeO
  33. The crystal structure of (E)-1-ferrocenyl-3-(4-isopropylphenyl)prop-2-en-1-one, C22H22FeO
  34. Crystal structure of 6-hydroxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one, C10H10O4
  35. The crystal structure of (2E,4E)-1-ferrocenyl-5-phenylpenta-2,4-dien-1-one, C21H18FeO
  36. Crystal structure of alaninato-κ2N,O-bis(hydroxylamido-κ2N,O)-oxido-vanadium(V), C3H10N3O5V
  37. Crystal structure of catena-poly[aqua-bis[μ2-6-(1H-imidazol-1-yl)nicotinato-κ2 N,O]copper(II)], C18H14N6O5Cu
  38. Crystal structure of diethyl 4,6-diphenyl-1,9-di-p-tolylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,5(2H)-dicarboxylate, C42H42N2O4
  39. The crystal structure of cobalt cadmium bis(hydrogenphosphate) bis(phosphate(V)) tetrahydrate, H10O20P4Co3.14Cd1.86
  40. Crystal structure of dimethyl 1,4,6,9-tetraphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,7(2H)-dicarboxylate, C38H34N2O4
  41. Crystal structure of (Z)-4-(furan-2-yl((4-iodophenyl)amino)methylene)-5-methyl-2(p-tolyl)-2,4-dihydro-3H-pyrazol-3-one, C21H16I N3O2
  42. Crystal structure of (E)-1-(4-(3,5-dimethoxystyryl)phenyl)-7-ethylheptanedioate, C25H30O6
  43. Crystal structure of 6-bromo-2-(4-chlorophenyl)chroman-4-one (6-bromo-4′-chloroflavanone), C15H10BrClO2
  44. The crystal structure of 2-(benzhydryloxy)-3-nitropyridine, C18H14N2O3
  45. The crystal structure of 1,3(4,1)-dipyridin-1-iuma-2(1,8)-diethynylanthracena-5(1,3)-benzenacyclohexaphane-11,31-diium bis(hexafluoridophosphate), C36H24F12N2P2
  46. Crystal structure of 3,6-di-tert-butyl-1-iodo-9-methyl-8-(pyren-1-ylethynyl)-9H-carbazole, C39H34IN
  47. The cocrystal 2-(dimethylammonio)-5-nitrobenzoate – 2-(dimethylamino)-5-nitrobenzoic acid, C9H10N2O4
  48. Crystal structure of 5-nitroquinazolin-4(3H)-one, C8H5N3O3
https://doi.org/10.1515/ncrs-2022-0064
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Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-(4-imidazol-1-yl-phenyl)-(2-methoxy-benzylidene)-amine monohydrate, C17H17N3O2
  4. Crystal structure of 6-methyl-3-(pyrrolidine-1-carbonyl)-2H-chromen-2-one, C15H15N1O3
  5. Crystal structure of 4-methyl-4-nitropentanoic acid, C6H11NO4
  6. The crystal structure of (E)-3-(furan-2-yl)acrylonitrile, C7H5NO
  7. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)-1H-pyrazole-4-carboxamide monohydrate, C23H26F2N4O3
  8. Crystal structure of 2-(4-bromobenzyloxy)-6-chloropyridine, C12H9BrClNO
  9. Crystal structure of N-(4-bromo-2,6-dichloro-phenyl)pyrazin-2-amine, C10H6BrCl2N3
  10. Crystal structure of (E)-1-(2–nitrophenyl)-3-phenylprop-2-en-1-one, C15H11NO3
  11. The crystal structure of (E)-3-chloro-2-(2-(4-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  12. Crystal structure of (E)-amino(2-(thiazol-2-ylmethylene)hydrazineyl)methaniminium nitrate, C10H16N12O6S2
  13. Crystal structure of 9-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C15H18N4O
  14. The crystal structure bis(dimethylsulfoxide-κ1O)-dipyridine-κ1 N-bis(m2-(Z)-3-methyl-2-oxido-N-((Z)-oxido(phenyl)methylene)benzohydrazonato-κ5)trinickel(II) - dimethylsulfoxide (1/2), C48H56N6Ni3O10S4
  15. Crystal structure of bis(bis(triphenylphosphine)iminium) tetradecacarbonyltetratelluridopentaferrate(2-), (PPN)2[Fe5Te4(CO)14]
  16. Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one, C15H14O2S
  17. The crystal structure of [(1,10-phenanthroline-κ2 N,N)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)nickel(II)] monohydrate, C36H26N4O5Ni
  18. Crystal structure of 3,3′-(pyridine-2,6-diylbis(methylene))bis(1-propyl-1H-imidazol-3-ium) ditetrafluoroborate, C19H27B2F8N5
  19. The crystal structure of (E)-1-(4-aminophenyl)-3-(p-tolyl)prop-2-en-1-one, C16H15NO
  20. The crystal structure of poly[(μ2-terephthalato-κ4O,O′: O″,O‴)-(μ4-terephthalato-κ4O:O′:O″:O‴)-{μ4-(1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ4O:O′:O″,O‴)}dicadmium(II)] – water – acetronitrile (1/2/2), C38H36N14O10Cd2
  21. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)cobalt(II)–water–N,N-dimethylformamide(1/2/1), C27H31N3O9Co
  22. The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid – 4,4′-bipyridine, C8H8O4·C10H8N2
  23. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)cobalt(II)], C32H22Br2CoN4O4
  24. Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione – methanol (1/1), C11H13N5S
  25. The crystal structure of (Z)-4-bromo-6-(((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)methylene)cyclohexa-2,4-dien-1-one monohydrate, C11H16BrNO5
  26. Crystal structure of bis(tetrapropylammonium) nonaselenidotetrastannate(IV), (Pr4N)2[Sn4Se9]
  27. Crystal structure of 2,6-di-tert-butyl-4-(4-chlorobenzylidene)cyclohexa-2,5-dien-1-one, C21H25ClO
  28. Crystal structure of (2,2′-((naphthalen-1-ylmethyl)azanediyl)diacetato-κ3 N,O,O′)-(1,10-phenanthroline-κ2 N,N′)-copper(II) trihydrate, CuC27H27N3O7
  29. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylato-κ2N,O)-bis(1H-pyrazol-3-ylamine-κ2 N:N)dicobalt(II) dihydrate, C27H23N5O5Co
  30. The crystal structure of bis((E)-2-((tert-butylimino)methyl)-4-chlorophenolato-κ2N,O)zinc(II), C22H26Cl2N2O2Zn
  31. The crystal structure of poly[diaqua-(μ3-5-nitrobenzene-1,2,3-tricarboxylato-κ3O:O′:O′)-(μ2-4,4′-dipyridylamine-κ2N:N′)copper(II)], C38H30Cu3N8O20
  32. The crystal structure of (E)-1-ferrocenyl-3-(naphthalen-1-yl)prop-2-en-1-one, C23H18FeO
  33. The crystal structure of (E)-1-ferrocenyl-3-(4-isopropylphenyl)prop-2-en-1-one, C22H22FeO
  34. Crystal structure of 6-hydroxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one, C10H10O4
  35. The crystal structure of (2E,4E)-1-ferrocenyl-5-phenylpenta-2,4-dien-1-one, C21H18FeO
  36. Crystal structure of alaninato-κ2N,O-bis(hydroxylamido-κ2N,O)-oxido-vanadium(V), C3H10N3O5V
  37. Crystal structure of catena-poly[aqua-bis[μ2-6-(1H-imidazol-1-yl)nicotinato-κ2 N,O]copper(II)], C18H14N6O5Cu
  38. Crystal structure of diethyl 4,6-diphenyl-1,9-di-p-tolylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,5(2H)-dicarboxylate, C42H42N2O4
  39. The crystal structure of cobalt cadmium bis(hydrogenphosphate) bis(phosphate(V)) tetrahydrate, H10O20P4Co3.14Cd1.86
  40. Crystal structure of dimethyl 1,4,6,9-tetraphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,7(2H)-dicarboxylate, C38H34N2O4
  41. Crystal structure of (Z)-4-(furan-2-yl((4-iodophenyl)amino)methylene)-5-methyl-2(p-tolyl)-2,4-dihydro-3H-pyrazol-3-one, C21H16I N3O2
  42. Crystal structure of (E)-1-(4-(3,5-dimethoxystyryl)phenyl)-7-ethylheptanedioate, C25H30O6
  43. Crystal structure of 6-bromo-2-(4-chlorophenyl)chroman-4-one (6-bromo-4′-chloroflavanone), C15H10BrClO2
  44. The crystal structure of 2-(benzhydryloxy)-3-nitropyridine, C18H14N2O3
  45. The crystal structure of 1,3(4,1)-dipyridin-1-iuma-2(1,8)-diethynylanthracena-5(1,3)-benzenacyclohexaphane-11,31-diium bis(hexafluoridophosphate), C36H24F12N2P2
  46. Crystal structure of 3,6-di-tert-butyl-1-iodo-9-methyl-8-(pyren-1-ylethynyl)-9H-carbazole, C39H34IN
  47. The cocrystal 2-(dimethylammonio)-5-nitrobenzoate – 2-(dimethylamino)-5-nitrobenzoic acid, C9H10N2O4
  48. Crystal structure of 5-nitroquinazolin-4(3H)-one, C8H5N3O3
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Heruntergeladen am 5.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2022-0064/html
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