Startseite Crystal structure of 6,6′-((pentane-1,3-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dibromolphenolato-κ4 N,N′,O,O′)copper(II),) C19H16Br4CuN2O2
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Crystal structure of 6,6′-((pentane-1,3-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dibromolphenolato-κ4 N,N′,O,O′)copper(II),) C19H16Br4CuN2O2

  • Rui Duan , Wang Man , Huang Meifen , Xun Ma und Qiong Wu ORCID logo EMAIL logo
Veröffentlicht/Copyright: 17. November 2021

Abstract

C19H16Br4CuN2O2: monoclinic, P21/c (no. 14), a = 10.2649(3) Å, b = 10.1903(3) Å, c = 21.2494(6) Å, β = 100.522(1)°, V = 2185.36(11) Å3, Z = 4, wR 2 = 0.0730, T = 169.0 K.

CCDC no.: 2113000

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: Block, clear brownish brown
Size: 0.20 × 0.18 × 0.16 mm
Wavelength: Mo K α radiation (0.71073 Å)
μ: 8.33 mm−1
Diffractometer, scan mode: CCD area detector, φ and ω-scans
θ max, completeness: 26.4°, >99%
N(hkl)measured, N(hkl)unique, R int: 24444, 4468, 0.078
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3154
N(param)refined: 254
Programs: CrysAlisPRO [1], OLEX2 [2], SHELX [3, 4]
Table 2:

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

Atom x y z U iso*/U eq
Br1 0.02669 (6) 0.12909 (5) 0.08882 (2) 0.03108 (15)
Br2 −0.35796 (6) 0.20353 (5) −0.13526 (2) 0.03574 (16)
Br3 0.43141 (5) 0.42199 (5) 0.22468 (2) 0.02917 (14)
Br4 0.46623 (6) 0.78530 (7) 0.42967 (3) 0.04799 (19)
Cu1 0.00102 (6) 0.58628 (5) 0.13835 (3) 0.02068 (15)
O1 −0.0103 (3) 0.4156 (3) 0.10207 (14) 0.0236 (8)
O2 0.1621 (3) 0.5360 (3) 0.19085 (15) 0.0247 (8)
N1 −0.1228 (4) 0.6607 (4) 0.06701 (18) 0.0229 (10)
N2 −0.0379 (4) 0.7205 (4) 0.19815 (18) 0.0211 (9)
C1 −0.1694 (5) 0.4589 (4) 0.0059 (2) 0.0204 (11)
C2 −0.0856 (5) 0.3770 (4) 0.0497 (2) 0.0194 (11)
C3 −0.0888 (5) 0.2409 (4) 0.0333 (2) 0.0212 (11)
C4 −0.1684 (5) 0.1904 (5) −0.0197 (2) 0.0246 (12)
H4 −0.169288 0.098751 −0.027989 0.029*
C5 −0.2480 (5) 0.2752 (5) −0.0614 (2) 0.0264 (12)
C6 −0.2477 (5) 0.4078 (5) −0.0500 (2) 0.0239 (12)
H6 −0.300209 0.464881 −0.079703 0.029*
C7 −0.1786 (5) 0.5984 (4) 0.0164 (2) 0.0216 (11)
H7 −0.230127 0.648477 −0.016824 0.026*
C8 −0.1428 (5) 0.8025 (4) 0.0716 (2) 0.0274 (12)
H8A −0.192169 0.835288 0.030184 0.033*
H8B −0.055531 0.846820 0.080081 0.033*
C9 −0.2190 (6) 0.8376 (5) 0.1245 (2) 0.0329 (13)
H9A −0.314071 0.819609 0.108566 0.039*
H9B −0.209715 0.933084 0.132519 0.039*
C10 −0.1772 (5) 0.7656 (5) 0.1888 (2) 0.0255 (12)
H10 −0.186081 0.827901 0.224071 0.031*
C11 0.0407 (5) 0.7512 (5) 0.2511 (2) 0.0243 (12)
H11 0.008057 0.811626 0.278566 0.029*
C12 0.1727 (5) 0.7017 (5) 0.2720 (2) 0.0206 (11)
C13 0.2243 (5) 0.5969 (5) 0.2409 (2) 0.0208 (11)
C14 0.3558 (5) 0.5579 (5) 0.2672 (2) 0.0231 (11)
C15 0.4286 (5) 0.6130 (5) 0.3218 (2) 0.0266 (12)
H15 0.516021 0.583692 0.338205 0.032*
C16 0.3709 (5) 0.7127 (5) 0.3524 (2) 0.0266 (12)
C17 0.2465 (5) 0.7571 (5) 0.3282 (2) 0.0292 (13)
H17 0.209287 0.825860 0.349379 0.035*
C18 −0.2653 (5) 0.6457 (5) 0.1940 (2) 0.0274 (12)
H18A −0.358945 0.674274 0.187774 0.033*
H18B −0.256729 0.582909 0.159458 0.033*
C19 −0.2294 (6) 0.5766 (6) 0.2583 (2) 0.0398 (15)
H19A −0.289962 0.502773 0.259780 0.060*
H19B −0.236802 0.638477 0.292742 0.060*
H19C −0.138210 0.543872 0.263744 0.060*

Source of material

The structure was solved with the OLEX2 program [2] as an interface together with the SHELXT and SHELXL programs [3, 4]. All H atoms were placed in geometrically idealized positions and refined using a riding model, with C–H = 0.98(methylene), 0.95 Å (benzene), and with U iso(H) = 1.2 U eq(C) for H atoms.

Experimental details

3,5-dibromosalicylaldehyde (0.0279 g, 0.10 mmol) was dissolved in methanol (30 mL) with stirring, adding 1,3-diaminopentane (0.05 mmol). The mixture was stirred and refluxed at 80 °C for 3 h. The solvent was removed by rotary evaporator to give yellow the powdered was dissolved in a mixture containing 20 mL metanol and 10 mL ethanol. Then, 0.1 g copper nitrate was add to the above solution and the resulting dark green mixture was further stirred at room temperature overnight. Dark brown crystals of the title compound were isolated after two weeks.

Comment

Schiff base is a kind of excellent ligand for 3d and 4f metal ion owing to its characteristic –C=N– group, in which the N atom has a lone pair of electrons, creating an electron-rich chemical environment [5, 6]. The introduction of electron-rich atoms such as O, N and S that favorable to the space environment of –C=N– structure into Schiff base can create more favorable electron-rich chemical environment for coordination between Schiff base and metal ions. As a part of our current research on the exploration of the regulating effect of Schiff base ligands on transition metal complexes [7, 8], we report herein a new.

Single-crystal X-ray diffraction reveals that there is one crystallography independent Cu(II) complex in the asymmetric unit. The central Cu(II) exhibits tetra-coordinated environment which is defined by N2O2 from the Schiff-base ligand. The bond lengths of Cu–O(N) are in the range of 1.889(3)–1.957(4) Å and bond angles of O(N)–Cu–O varies from 88.47(23) to 160.54(26)°, which is compared favorably with the corresponding values observed in salen-type Cu(II) analogous [9, 10].

The dihedral angle calculated between the planes of the two benzene rings is 38.135(16)°.


Corresponding author: Qiong Wu, Department of Chemical Science and Technology, Kunming University, Yunnan, Kunming 65200, P. R. China, E-mail:

Funding source: Fund for Less Developed National Nature Science Foundation of China

Award Identifier / Grant number: 31760257, 21761017

Funding source: Joint Basic Research Program (partial) of Yunnan Provincial Undergraduate Universities

Award Identifier / Grant number: 2017FH001-002

Funding source: Program for Innovative Research Team (in Science and Technology) in Universities of Yunnan Province

Award Identifier / Grant number: IRTSTYN

Funding source: Recruitment Program of Yunnan Province Experts Provincial Young Talents

Award Identifier / Grant number: 2019HB098

Funding source: Ten-Thousand Talents Program of Yunnan Province

Award Identifier / Grant number: YNWR-QNBJ-2018-273

  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 Fund for Less Developed National Nature Science Foundation of China (No. 31760257, 21761017) as well as the Joint Basic Research Program (partial) of Yunnan Provincial Undergraduate Universities (2017FH001–002), the Program for Innovative Research Team (in Science and Technology) in Universities of Yunnan Province (IRTSTYN), the Recruitment Program of Yunnan Province Experts Provincial Young Talents (2019HB098) and the Ten–Thousand Talents Program of Yunnan Province (YNWR–QNBJ-2018–273).

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

References

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Received: 2021-09-29
Accepted: 2021-11-05
Published Online: 2021-11-17
Published in Print: 2022-02-23

© 2021 Rui Duan 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)-7-hydroxy-2-((6-methoxypyridin-3-yl)methylene)-3, 4-dihydronaphthalen-1(2H)-one, C17H15NO3
  4. Crystal structure of (E)-7-methoxy-2-((2-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1 (2H)-one, C18H17NO3
  5. The crystal structure of N 6,N 6′-di(pyridin-2-yl)-[2,2′-bipyridine]-6,6′-diamine, C20H16N6
  6. The crystal structure of {N 1,N 2-bis[2,4-dimethyl-6-(4-(tert-butyl)phenyl)(phenyl)methyl]acenaphthylene-1,2-diimino-κ2 N, N′}-dibromido-nickel(II) – dichloromethane(1/2), C64H64Br2Cl4N2Ni
  7. Synthesis and crystal structure of nonacarbonyltris[(2-thia-1,3,5-triaza-7-phosphatricylco[3.3.1.1]decane-κ1 P)-2,2-dioxide]triruthenium(0) – acetonitrile (7/6), C25.71H32.57N9.86O15P3S3Ru3
  8. A new polymorph of 1-(4-nitrophenyl)-1H-benzimidazole (C13H9N3O2)
  9. The crystal structure of 2,2′-((1E,1′E)-(naphthalene-2,3 diylbis(azanylylidene)) bis(methanylylidene))bis(4-methylphenol), C26H22N2O2
  10. The crystal structure of bis(μ2-iodido)-bis(η6-benzene)-bis(iodido)-diosmium(II), C12H12I4Os2
  11. Redetermination of the crystal structure of bis{hydridotris(3,5-dimethylpyrazol-1-yl-κN 3)borato}copper(II), C30H44B2CuN12
  12. Crystal structure of (E)-3-((4-(tert-butyl)phenyl)thio)-4-hydroxypent-3-en-2-one, C15H20O2S
  13. Crystal structure of 2,2′-(p-tolylazanediyl)bis(1-phenylethan-1-one), C23H21NO2
  14. Redetermination of the crystal structure of the crystal sponge the poly[tetrakis(μ3-2,4,6-tris(pyridin-4-yl)-1,3,5-triazine)-dodecaiodidohexazinc(II) nitrobenzene solvate], C72H48I12N24Zn6⋅10(C6H5NO2)
  15. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(6-methylpyridin-2-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C44H45N5O2
  16. Crystal structure of (E)-7-fluoro-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O1
  17. Crystal structure of tetrabutylammonium sulfanilate – 1-(diaminomethylene)thiourea (1/2)
  18. Crystal structure of [2,2′-{azanediyl)bis[(propane-3,1-diyl)(azanylylidene)methylylidene]} bis(3,5-dichlorophenolato)-κ2O,O′]-isothiocyanato-κN-iron(III), C21H19Cl4FeN4O2S
  19. Crystal structure of (4-chlorophenyl)(4-hydroxyphenyl)methanone, C13H9ClO2
  20. Crystal structure of 6,6′-((pentane-1,3-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dibromolphenolato-κ4 N,N′,O,O′)copper(II),) C19H16Br4CuN2O2
  21. Chlorido-(2,2′-(ethane-bis(5-methoxyphenolato))-κ4 N,N,O,O′)manganese(III) monohydrate, C19H18Cl2CuN2O2
  22. Crystal structure of 2,6-di-tert-butyl-4-(4-methoxybenzylidene)cyclohexa-2,5-dien-1-one, C22H28O2
  23. Crystal structure of [6,6′-(((2,2-dimethylpropane-1,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato)-κ4N,N′,O,O′]copper(II)
  24. Crystal structure of 2-chloro-3-((thiophen-2-ylmethyl)amino)naphthalene-1,4-dione, C30H20O4N2Cl2S2
  25. Crystal structure of bis{hydridotris(3-trifluoromethyl-5-methylpyrazolyl-1-yl)borato-κN 3}manganese(II), C30H26B2F18MnN12
  26. Crystal structure of 1-(2-methylphenyl)-2-(2-methylbenzo[b]thienyl)-3,3,4,4,5,5-hexafluorocyclopent-ene, C21H14F6S
  27. Crystal structure of 2-(3-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  28. Crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium chloride – chloroform (1/1), C21H23Cl4I2N3
  29. Crystal structure of azido-k1 N-{6,6′-((((methylazanediyl)bis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,4-dibromophenolato)k5 N,N′,N″,O,O′}cobalt(III)-methanol (1/1)), C21H23Br4CoN6O3
  30. The crystal structure of 2-(4-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  31. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C9H14F12N4P2
  32. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(pyren-1-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C54H48N4O2
  33. Crystal structure of poly[bis(μ2-2,6-bis(1-imidazoly)pyridine-κ2 N,N′)-bis(thiocyanato-κ1 N)copper(II)] dithiocyanate, C24H18CuN12S2
  34. Cones with a three-fold symmetry constructed from three hydrogen bonded theophyllinium cations that coat [FeCl4] anions in the crystal structure of tris(theophyllinium) bis(tetrachloridoferrate(III)) chloride trihydrate, C21H33Cl9Fe2N12O9
  35. Crystal structure of 14-O-[(4-(4-hydroxypiperidine-1-yl)-6-methylpyrimidine-2-yl)thioacetyl]-mutilin monohydrate, C32H49N3O6S
  36. The crystal structure of (E)-3-chloro-2-(2-(4-methylbenzylidene)hydrazinyl)pyridine, C13H12ClN3
  37. The crystal structure of 4-phenyl-4-[2-(pyridine-4-carbonyl)hydrazinylidene]butanoic acid, C16H15N3O3
  38. The crystal structure of 6-amino-5-carboxypyridin-1-ium pentaiodide monohydrate C6H9I5N2O3
  39. Crystal structure of bis(μ3-oxido)-bis(μ2-2-formylbenzoato-k2O:O′)-bis(2-(dimethoxymethyl)-benzoato-κO)-oktakismethyl-tetratin(IV)
  40. Crystal structure of 2-((E)-(((E)-2-hydroxy-4-methylbenzylidene) hydrazineylidene)methyl)-4-methylphenol, C16H16N2O2
  41. Crystal structure of (E)-amino(2-((5-methylfuran-2-yl)methylene)hydrazinyl) methaniminium nitrate monohydrate, C14H26N10O10
  42. The crystal structure of N′-(2-chloro-6-hydroxybenzylidene)thiophene-2-carbohydrazide monohydrate, C12H11ClN2O3S
  43. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)zinc(II)], C64H44Br4N8O8Zn2
  44. The crystal structure of catena-poly[(1-(4-carboxybenzyl)pyridin-1-ium-4-carboxylato-κ1O)-(μ2-oxalato-κ4 O:O′:O″:O‴)dioxidouranium(VI)], C16H11NO10U
  45. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-phenylfuran, C22H21BrO2
  46. Halogen bonds in the crystal structure of 4,3′:5′,4″-terpyridine — 1,3-diiodotetrafluorobenzene (1/1), C21H11F4I2N3
  47. Crystal structure of 2-(1H-indol-3-yl)ethan-1-aminium 2-(4-acetylphenoxy)acetate, C20H22N2O4
  48. Chalcogen bonds in the crystal structure of 4,7-dibromo-2,1,3-benzoselenadiazole, C6H2Br2N2Se
  49. The crystal structure of 1,4-bis((1H-benzimidazol-2-yl)methyl)-piperazine-2,5-dione dihydrate, C20H22N6O4
  50. The crystal structure of C19H20O8
  51. The crystal structure of KNa3Te8O18·5H2O exhibiting a 2[Te4O9]2− layer
  52. Erratum
  53. Erratum to: Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
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