Home {6,6′-((1E,1′E)-((2,2-dimethylpropane-1,3-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(2-bromo-4-chlorophenolate)-κ4N,N′,O,O′}copper(II), C19H16Br2Cl2CuN2O2
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{6,6′-((1E,1′E)-((2,2-dimethylpropane-1,3-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(2-bromo-4-chlorophenolate)-κ4N,N′,O,O′}copper(II), C19H16Br2Cl2CuN2O2

  • Qiong Wu ORCID logo EMAIL logo , Guojun Yu , Jiao Yang and Qiuling Yang
Published/Copyright: September 12, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 6

Abstract

C19H16Br2Cl2CuN2O2, monoclinic, P21/n (no. 14), a = 12.4679(2)Å, b = 8.61760(10) Å, c = 19.7854(3) Å, β = 97.1610(10)°, V = 2109.23(5) Å3, Z = 4, R gt (F) = 0.0325, wR ref (F 2) = 0.0865, T = 170.0 K.

CCDC no.: 2178589

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: Green block
Size: 0.07 × 0.02 × 0.02 mm
Wavelength: CuKα radiation (1.54184 Å)
μ: 8.39 mm−1
Diffractometer, scan mode: XtaLAB Synergy, ω
θ max, completeness: 75.9°, 99%
N(hkl)measured, N(hkl)unique, R int: 13085, 4118, 0.042
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3541
N(param)refined: 255
Programs: Bruker [1], Olex2 [2], SHELX [3, 4]
Table 2:

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

Atom x y z U iso*/U eq
Br1 0.16560 (2) 0.17648 (4) 0.56144 (2) 0.03300 (10)
Br2 0.24719 (3) 0.30328 (5) 0.29005 (2) 0.04827 (13)
Cu1 0.51776 (3) 0.26844 (5) 0.48725 (2) 0.02739 (12)
Cl1 0.52360 (8) 0.67820 (12) 0.16746 (5) 0.0505 (2)
Cl2 0.37569 (7) −0.12136 (14) 0.78707 (5) 0.0590 (3)
O1 0.39415 (16) 0.1964 (3) 0.52597 (11) 0.0307 (5)
O2 0.43015 (17) 0.3111 (3) 0.40348 (11) 0.0317 (5)
N1 0.61990 (19) 0.1549 (3) 0.55246 (13) 0.0284 (5)
N2 0.6319 (2) 0.4092 (3) 0.46741 (13) 0.0292 (5)
C1 0.4885 (2) 0.0659 (4) 0.62409 (15) 0.0294 (6)
C2 0.3945 (2) 0.1264 (3) 0.58419 (15) 0.0263 (6)
C3 0.2958 (2) 0.1026 (4) 0.61209 (15) 0.0279 (6)
C4 0.2890 (3) 0.0311 (4) 0.67299 (16) 0.0340 (7)
H4 0.2220 0.0205 0.6897 0.041*
C5 0.3833 (3) −0.0261 (4) 0.70984 (17) 0.0384 (7)
C6 0.4815 (3) −0.0101 (4) 0.68603 (17) 0.0361 (7)
H6 0.5442 −0.0503 0.7113 0.043*
C7 0.5949 (2) 0.0759 (4) 0.60271 (16) 0.0302 (6)
H7 0.6505 0.0192 0.6280 0.036*
C8 0.7303 (2) 0.1444 (4) 0.53365 (17) 0.0315 (6)
H8A 0.7262 0.1063 0.4867 0.038*
H8B 0.7708 0.0676 0.5632 0.038*
C9 0.7936 (2) 0.2983 (4) 0.53895 (16) 0.0317 (6)
C10 0.7177 (3) 0.4376 (4) 0.52387 (16) 0.0326 (7)
H10A 0.6845 0.4628 0.5649 0.039*
H10B 0.7602 0.5277 0.5128 0.039*
C11 0.6353 (2) 0.4815 (4) 0.41106 (16) 0.0302 (6)
H11 0.6963 0.5438 0.4078 0.036*
C12 0.5540 (2) 0.4761 (4) 0.35195 (15) 0.0286 (6)
C13 0.4557 (2) 0.3920 (3) 0.35287 (15) 0.0275 (6)
C14 0.3817 (2) 0.4049 (4) 0.29234 (16) 0.0320 (6)
C15 0.4031 (3) 0.4876 (4) 0.23614 (16) 0.0332 (7)
H15 0.3525 0.4899 0.1967 0.040*
C16 0.5003 (3) 0.5679 (4) 0.23806 (16) 0.0340 (7)
C17 0.5742 (2) 0.5634 (4) 0.29518 (16) 0.0319 (7)
H17 0.6391 0.6193 0.2964 0.038*
C18 0.8747 (3) 0.2922 (5) 0.4867 (2) 0.0465 (9)
H18A 0.9179 0.1986 0.4936 0.070*
H18B 0.9215 0.3823 0.4923 0.070*
H18C 0.8358 0.2917 0.4410 0.070*
C19 0.8533 (3) 0.3203 (5) 0.61002 (19) 0.0463 (9)
H19A 0.8025 0.3126 0.6433 0.069*
H19B 0.8872 0.4218 0.6133 0.069*
H19C 0.9082 0.2407 0.6190 0.069*

Source of material

3–Bromosalicylaldehyde (0.100 g, 0.5 mmol) and ethylenediamine (0.030 g, 0.5 mmol) were dissolved in a mixture of 20 mL ethanol. The Schiff base solution was stirred at room temperature for 24 h. After this, copper(II) nitrate (0.75 mmol) was added to the above solution and the obtained black mixture was further stirred for 24 h and filtered. The acquired black filtrate was sealed in a beaker with parafilm and kept undisturbed at room temperature. The black block crystals of the title compound were afforded after one month by slow evaporation.

Experimental details

X-ray single crystal data was collected on a Bruker SMART APEX II diffractometer with rotating anode source (MoKα radiation, λ = 0.71073 Å). Data reduction was performed using the program SAINT and empirical absorption corrections were made using SADABS [1]. 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 0.97 Å (methyl); U iso(H) values were set 1.2 times for H atoms on methylene and benzene.

Comment

It is of significance to develop complexes via ligand substitution with different halogen atoms and study the relationship between structure and properties [5, 6]. Copper based complexes have potential applications in molecular catalysis, biosensors and medicine [7, 8]. The structures of copper complexes can be enriched by connecting copper ions with different halogenated Schiff-base ligands [9, 10]. Herein as a part of our current research on the exploration of the regulating effect of Schiff base metal complexes, we report a new Cu(II) complex.

The asymmetric unit is composed of one title complex (see the figure). The coordination environment of the ion center is defined by two oxygen atoms and two nitrogen atoms.

It should not kept unmentioned that there is an isomorphous structure to the title struture in which the bromo substituents are exchanged by chloro substituents [11] and nickel replaced by copper.

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

Funding source: National Nature Science Foundation of China

Award Identifier / Grant number: 31760257, 21761017

Funding source: Program for Innovative Research Team (in Science and Technology) in the 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 funded by National Nature Science Foundation of China (No. 31760257, 21761017), the Program for Innovative Research Team (in Science and Technology) in the 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: 2022-06-14
Accepted: 2022-08-26
Published Online: 2022-09-12
Published in Print: 2022-12-16

© 2022 the author(s), published by De Gruyter, Berlin/Boston

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

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https://doi.org/10.1515/ncrs-2022-0296
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 1,5-bis(4-chlorophenyl)-3-(3-methylphenyl)pentane- 1,5-dione, C48H40Cl4O4
  4. Crystal structure of (bis(1,10-phenanthroline-κ 2 N,N′))-(3,5-dinitrosalicylato-κ 2 O,O′)nickel(II), C31H18N6NiO7
  5. Crystal structure of {N,N′-bis(4-fluoro-salicylaldehyde)-3,6-dioxa-1,8-diaminooctane-κ4 O,N,N′,O′}zinc(II), C20H20F2N2O4Zn
  6. [5-Bromo-2-(2-(dimethylamino)ethyliminomethyl)phenolato-κ3 N,N′,O]-isothiocyanato-nickel(II), C12H14BrN3NiOS
  7. Crystal structure of 9-bromo-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin- 2-amine, C18H15BrN4O
  8. The crystal structure of imidazolium nitrate, C3H5O3N3
  9. Crystal structure of diiodido-bis(6,6′-dimethoxy-2,2′-(ethane-1,2-diylbis(nitrilomethanylylidene)) diphenolato)tricadmium(II), C36H36Cd3I2N4O8
  10. Crystal structure of [diaqua-bis(2-((1H-tetrazol-1-yl)methyl)-5-carboxy-1H-imidazole-4-carboxylato-κ2 N,O) manganese(II)] dihydrate, C14H18MnN12O12
  11. Crystal structure of Diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-k4 O,O′,N,N′)]iron(II), C13H14FeN4O10
  12. Crystal structure of poly[dimethanol-κ1O-(µ2-(E)-2-((2-oxidobenzylidene)amino)acetato)-(µ3-(E)-2-((2-oxidobenzylidene)amino)acetato)dicadmium(II)], C20H22Cd2N2O8
  13. Crystal structure of N 2,N 6-bis(2-(((E)-quinolin-8-ylmethylene)amino)phenyl)pyridine-2,6-dicarboxamide, C39H27N7O2
  14. An I 6 2 − anion in the crystal structure of theophyllinium triiodide monohydrate, C7H11I3N4O3
  15. The crystal structure of poly[6,6′-oxybis(4-(pyridin-1-ium-1-yl)-1,3,5,2,4,6-trioxatriborinan-2-olate)], [B6O9](C5H5N)2
  16. The crystal structure of (carbonato κ2 O,O′)(2-oxopyridin-1(2H)-olato-κN)tris(trimethylphosphine)rhodium(III) water solvate, C15H33NO5P3Rh
  17. The crystal structure of dibromido-bis((RS)-2-(4-chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile-κ1 N)zinc(II), C30H34Br2Cl2N8Zn
  18. Synthesis and crystal structure of 3-(((7-hydroxy-3-(4-hydroxy-3,5-dinitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)(nitroso)amino)propanoic acid, C19H14N4O11
  19. The crystal structure of 3-((4-chloro-N-(2-methoxyethyl)benzamido)methyl)phenyl methanesulfonate, C18H20ClNO5S
  20. Crystal structure of di([1,1′:3′,1″-terphenyl]-2′-yl)tellane, C36H26Te
  21. The crystal structure of diaqua-bis(pyrazolo[1,5-a]-pyrimidine-3-carboxylato-κ2 N,O)zinc(II), C14H12N6O6Zn
  22. Crystal structure of N′,N‴-((1E,2E)-1,2-diphenylethane-1,2-diylidene)bis(4-methylbenzohydrazide) – water – methanol (1/1/1), C31H32N4O4
  23. Crystal structure of 3-((2,4-dichlorobenzyl)thio)-5-methyl-7-(trifluoromethyl)-[1,2,4]triazolo [4,3-c]pyrimidine, C14H9Cl2F3N4S
  24. Crystal structure of 3,5,6,7-tetramethoxy-3′,4′-methylenedioxy-flavone, C20H18O8
  25. Crystal structure of catena-poly[(5,5′-dimethyl-2,2′-bipyridine-κ 2 N,N′)-(μ 3-hydrogen-1,1′,1″-(1,3,5-triazine-2,4,6-triyl)tris(piperidine-4-carboxylato)- κ 5 O:O,O′:O″,O‴)-cadmium(II)], C33H40CdN8O6
  26. The crystal structure of 3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C9H17N3
  27. Crystal structure of [(1,4,7,10-tetraoxacyclododecane-κ 4 O,O′,O″, O‴)-tris(nitrato-κ 2 O,O′)gadolinium(III)], C8H16N3O13Gd
  28. The crystal structure of 2,2′-((pyridine-2,6-diylbis(methylene))bis(sulfanediyl))-bis(4,5-dihydro-1H-imidazol-3-ium) bromide, C13H19Br2N5S2
  29. Crystal structure of E-2-chloro-N′-(1-(5-chloro-2-hydroxyphenyl)propylidene)benzohydrazide, C16H14Cl2N2O2
  30. Crystal structure of 3-(adamantan-1-yl)-4-methyl-5-{[(4-nitrophenyl)methyl]sulfanyl}-4H-1,2,4-triazole, C20H24N4O2S
  31. The crystal structure of dimethanol-κ1O-(5,10,15,20-tetrakis(4-nitrophenyl)porphyrin-21,23-diido-κ4 O,O′,O″,O′″)manganese(III) trans-dicyanido-κ1C-bis(acetylacetonato-κ2 O,O′)ruthenium(III), C58H46N10O14RuMn
  32. The crystal structure of nitroxyl-κ N-{hydridotris(3-trifluoromethyl-5-methylpyrazolyl-1-yl-κN 3)borato}nickel(II), C15H13BF9N7NiO
  33. The crystal structure of [(2,2′-bipyridine-κ2 N,N)-bis(6-phenylpyridine-2-carboxylato- κ2 N,O)nickel(II)] monohydrate, C34H26N4O5Ni
  34. The crystal structure of 5-(2-fluoro-3-methoxyphenyl)-1-(2-fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione, C20H15F5N2O3
  35. The crystal structure of ethyl 2,3,5-trifluoro-4-(4-oxo-3,4-dihydropyridin-1(2H)-yl)benzoate, C14H12F3NO3
  36. [2,2′-{Ethane-1,2-diylbis[(azanylylidene)methanylylidene]}bis(3-bromo-2-hydroxyphenyl)]iron(III) nitrate, C20H12Br2CuN2O2
  37. The crystal structure of 1-(2-iodophenyl)-4-phenyl-1H-1,2,3-triazole, C14H10IN3
  38. Synthesis and crystal structure of 2-(2-oxo-2-(thiophen-2-yl)ethyl)-4H-chromen-4-one, C15H10O3S
  39. {6,6′-((1E,1′E)-((2,2-dimethylpropane-1,3-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(2-bromo-4-chlorophenolate)-κ4N,N′,O,O′}copper(II), C19H16Br2Cl2CuN2O2
  40. The crystal structure of N′-[bis(2-hydroxyphenyl)methylidene]pyridine-4-carbohydrazide, C19H15N3O3
  41. Crystal structure of 2-chloro-6-formylphenolato-κ2O,O′-(6,6′-(((2,2-dimethylpropane-1,3-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(2-chlorophenolato)κ4 N,N,O,O′)cobalt(III), C26H22Cl3CoN2O4
  42. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylate-κ 2 N,O)-bis(μ2-6-phenylpyridine-2-carboxylate-κ 2 O:O′)-bis(μ2-6-phenylpyridine-2-carboxylate-κ 3N,O:O)tetralead(II) C48H32N4O8Pb2
  43. The crystal structure of 3,7-dihydroxy-9-methoxy-4a-methyl-4aH-benzo[c] chromene-2,6-dione —dichloromethane (1/1), C16H14Cl2O6
  44. The crystal structure of (Z)-6-(((5-chloro-2-hydroxyphenyl)amino)methylene)- 4-nitrocyclohexa, C13H9ClN2O4
  45. Crystal structure of dichlorido-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1 N)zinc(II), C60H68O4N12Cl10Zn
  46. The crystal structure of 4-(2-bromoethoxy)-2-hydroxybenzaldehyde, C9H9BrO3
  47. The crystal structure of 5-azido-1-methyl-4-nitroimidazole, C4H4O2N6
  48. Crystal structure of dibromido-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II), C60H68O4N12Br2Cl8Zn
  49. Crystal structure of tetrasodium-bis(μ 2-oxido)-hexafluoro-didioxo-molybdenum(V), Na2(Mo2O4F6)
  50. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-4- hydroxybenzohydrazide-water (1/1), C14H13Cl1N2O4
  51. Crystal structure of (E)-N-(4-morpholinophenyl)-1-(quinolin-2-yl)methanimine, C20H19N3O
  52. The crystal structure of catena-poly[(1,10-phenanthroline-κ2 N,N′)-(μ3-2-hydroxybenzene-1,3-dicarboxylato-κ5 O,O′:O″,O‴:O‴)cadmium(II)], C20H12CdN2O5
  53. The crystal structure of 2,6-di-tert-butyl-4-(4-(methylthio)benzylidene)cyclohexa-2,5-dien-1-one, C22H28OS
  54. La3.65Mg30Sb1.07 as a disordered derivative of Th2Ni17-type structure
  55. Crystal structure of (E)-N-(4-morpholinophenyl)-1-(quinoxalin-2-yl)methanimine, C19H18N4O
  56. The crystal structure of 2,2′-(1,2-phenylenebis(methylene))bis(1,3-dimethylisothiouronium) bromide, C14H24Br2N4S2
  57. Crystal structure of tetraaqua-bis[4-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N]zinc(II), C18H20ZnN6O8
  58. Crystal structure of bis(tricarbonyl)-{(S)-(tert-butoxycarbonyl)(1-methoxy-1-oxo-3-sulfido-k2 S:S′-propan-2-yl)amido-k2N:N′}diiron(I) (Fe—Fe), C15H15Fe2NO10S
  59. Crystal structure of (E)-3-((4-chlorophenyl)thio)-4-hydroxypent-3-en-2-one, C11H11ClO2S
  60. The crystal structure of (E)-3′,6′-bis(diethylamino)-2-((5-(diethylamino)-2-hydroxybenzylidene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C39H45N5O3
  61. The crystal structure of 2-(4-methoxynaphthalen-1-yl)-4H-chromen-4-one, C20H14O3
  62. The crystal structure of trans-dichlorido-(ethylenediamine-κ 2 N,N′)-bis(triphenylphosphine-κ 1 P)ruthenium(II), C38H38Cl2N2P2Ru
  63. The double polymeric chain of catena-poly[(μ2-6-bromopyridine-3-carboxylato-κ2 O,O′) (6-bromopyridine-3-carboxylato-κ2 O,O′) (μ2-1,2-bis(4-pyridyl)ethylene-κ2 N:N′)cobalt(II)], C24H16CoBr2N4O4
  64. The crystal structure of tert-butyl 2-(4-(12-bromo [2.2]paracyclophanyl)carbamoyl)pyrrolidine-1-carboxylate, C26H31BrN2O3
  65. The crystal structure of (Z)-2-(2,3-dimethoxybenzylidene)naphtho[1,2-b]furan-3(2H)-one, C21H16O4
  66. Crystal structure of 2-hydroxy-1-tosylindolin-3-yl- 2-naphthoate, C26H21N1S1O5
  67. The crystal structure of 1-methyl-N-(1-methyl-1H-imidazole-2-carbonyl)-1H-imidazole-2-carboxamide, C10H11N5O2
  68. The crystal structure of (E)-2-((5-bromo-2-hydroxybenzylidene)amino)-3′,6′-bis(ethylamino)-2′, 7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one, C33H31BrN4O3
  69. The crystal structure of dimethanol-5,15-diphenylporphyrin-21,23-diido-κ4 N,Nʹ,Nʺ,Nʹʺ-manganese(III) trans-dicyanido-bis(acetylacetonato-κ2O,Oʹ)ruthenium(III), C46H42N6O6RuMn
  70. Crystal structure of 1,4,8,11-tetraazacyclotetradecane-1,8-diium bis(3,5-dicarboxybenzoate), C28H36N4O12
  71. Bifurcated halogen bonds in the crystal structure of 2,2′-bi(1,8-naphthyridine)—1,4-diiodotetrafluorobenzene (1/1), C22H10F4I2N4
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