Startseite Crystal structure of bis(4-bromo-2-(((3-bromopropyl)imino)methyl)phenolato-κ2N,O)-oxido-vanadium(IV), C20H20Br4N2O3V
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Crystal structure of bis(4-bromo-2-(((3-bromopropyl)imino)methyl)phenolato-κ2N,O)-oxido-vanadium(IV), C20H20Br4N2O3V

  • Wei Wei , Juan Xia , Wei-Ya Zhang , Heng-Qiang Zhang ORCID logo , Fu-Jian Fang , Yang Xin und Xiu-Jun Zheng EMAIL logo
Veröffentlicht/Copyright: 29. September 2021

Abstract

C20H20Br4N2O3V, monoclinic, P21/c (no. 14), a = 12.6011(10) Å, b = 16.5997(8) Å, c = 12.9206(12) Å, β = 119.006(11)°, V = 2363.7(4) Å3, Z = 4, R gt (F) = 0.0518, wR ref (F 2) = 0.1062, T = 153(2) K.

CCDC no.: 2110178

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: 0.21 × 0.20 × 0.18 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 7.21 mm−1
Diffractometer, scan mode: Xcalibur, φ and ω
θ max, completeness: 25.0°, >99%
N(hkl)measuredN(hkl)uniqueR int: 13114, 4152, 0.062
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2792
N(param)refined: 281
Programs: CrysAlisPRO [1], SHELX [2], WinGX/ORTEP [3], PLATON [4]
Table 2:

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

Atom x y z U iso*/U eq
Br1 0.83724 (8) 1.03500 (4) 0.19060 (8) 0.0663 (3)
Br2 0.09345 (6) 0.31912 (4) −0.02620 (7) 0.0533 (2)
Br3Aa 0.1145 (5) 0.8078 (6) 0.3151 (7) 0.0748 (18)
Br3Bb 0.1334 (10) 0.7774 (9) 0.3256 (6) 0.091 (2)
Br4 1.01107 (6) 0.62854 (4) 0.46765 (6) 0.0455 (2)
C1 0.7401 (5) 0.7283 (3) 0.2097 (5) 0.0310 (14)
H1 0.817775 0.721207 0.219818 0.037*
C2 0.6922 (5) 0.8086 (3) 0.1860 (5) 0.0276 (14)
C3 0.7709 (6) 0.8716 (4) 0.1938 (5) 0.0392 (16)
H3 0.850941 0.860512 0.214053 0.047*
C4 0.7290 (6) 0.9491 (4) 0.1717 (5) 0.0407 (17)
C5 0.6100 (7) 0.9674 (4) 0.1380 (5) 0.0432 (18)
H5 0.582808 1.020436 0.122137 0.052*
C6 0.5327 (6) 0.9069 (4) 0.1283 (5) 0.0407 (16)
H6 0.451814 0.918907 0.103447 0.049*
C7 0.5724 (6) 0.8271 (3) 0.1550 (5) 0.0354 (15)
C8 0.7507 (5) 0.5875 (3) 0.2356 (5) 0.0302 (14)
H8A 0.825148 0.596940 0.232740 0.036*
H8B 0.700683 0.551187 0.171465 0.036*
C9 0.7807 (5) 0.5483 (3) 0.3516 (5) 0.0357 (16)
H9A 0.705398 0.535403 0.351216 0.043*
H9B 0.822318 0.497891 0.357560 0.043*
C10 0.8575 (5) 0.5977 (4) 0.4590 (5) 0.0383 (16)
H10A 0.873834 0.567082 0.529135 0.046*
H10B 0.813373 0.645852 0.457699 0.046*
C11 0.2554 (5) 0.6137 (3) 0.1052 (5) 0.0307 (14)
H11 0.174267 0.624504 0.081002 0.037*
C12 0.2836 (5) 0.5337 (3) 0.0807 (5) 0.0281 (14)
C13 0.1914 (5) 0.4760 (3) 0.0390 (5) 0.0316 (14)
H13 0.112924 0.490402 0.020702 0.038*
C14 0.2179 (5) 0.3982 (4) 0.0254 (5) 0.0341 (15)
C15 0.3314 (5) 0.3756 (3) 0.0489 (5) 0.0310 (14)
H15 0.347331 0.321934 0.040746 0.037*
C16 0.4230 (5) 0.4323 (3) 0.0848 (5) 0.0338 (15)
H16 0.499274 0.417173 0.097088 0.041*
C17 0.4013 (5) 0.5122 (3) 0.1028 (5) 0.0301 (14)
C18 0.2788 (6) 0.7455 (4) 0.1776 (7) 0.055 (2)
H18A 0.191134 0.741046 0.139079 0.066*
H18B 0.299095 0.791159 0.143735 0.066*
C19 0.3315 (6) 0.7597 (5) 0.3171 (8) 0.084 (3)
H19A 0.319009 0.711308 0.351806 0.101*
H19B 0.418160 0.769198 0.353641 0.101*
C20 0.2766 (7) 0.8253 (5) 0.3423 (8) 0.086 (3)
H20A 0.275403 0.870800 0.294665 0.104*
H20B 0.327181 0.840010 0.424635 0.104*
N1 0.3306 (4) 0.6709 (3) 0.1568 (4) 0.0323 (12)
N2 0.6856 (4) 0.6650 (3) 0.2184 (4) 0.0260 (11)
O1 0.4910 (3) 0.5647 (2) 0.1400 (3) 0.0335 (10)
O2 0.4935 (3) 0.7703 (2) 0.1468 (3) 0.0372 (11)
O3 0.5665 (4) 0.6648 (2) 0.3545 (3) 0.0445 (11)
V1 0.51793 (9) 0.66669 (6) 0.21604 (9) 0.0291 (3)
  1. aOccupancy: 0.48 (2), bOccupancy: 0.52 (2).

Source of material

In a 250 ml round bottom flask containing 50 ml of absolute methanol were added 5 mmol of 3-bromopropyl-ammonium hydrochloride and 5 mmol of 5–bromo-2-hydroxy-benzaldehyde. Then 5 mmol of NaOH was dissolved in 2 ml H2O, were added to the above solution and the contents were refluxed for 3 h at 343 K. After cooling to room temperature, 12 ml methanol containing 2.5 mmol of vanadyl acetylacetonate were added. To this solution was added 30 ml trichloromethane and filtered off. The contents of the flask were refluxed with stirring for 3 h at 343 K. The green crystals that formed were filtered off after five days at room temperature.

Experimental details

Hydrogen atoms are positioned using the riding models of the SHELX system. Their U iso values were set to 1.2U eq of the parent atoms. One of Br atom is disordered over two positions in a 0.52:0.48 ratio.

Comment

Schiff base ligands play a central role in the coordination chemistry [5]. They have a variety of applications due to its structural features, including catalytic applications, biological roles, iglycogen metabolism, as well as insulin mimicking and organic synthesis [6], [7], [8], [9], [10]. In our previous publications, we studied the Schiff base complexes, which exhibit insulin mimicking, and catalytic activity in the epoxidation reaction [11, 12]. Halogenated organic compounds gives suitable properties for different uses such as synthetic intermediates and starting compounds, designer molecules for material science, industrial chemicals, and bioactive compounds [13]. In order to expand its application to Schiff base, we present in this paper the synthesis of a halogenated schiff base and the crystal structures of the title compound.

The molecular structure of the title compound with the atom-numbering scheme is illustrated in the figure. The crystallographic data showed that the vanadium (IV) ion was surrounded by two oxygen and two nitrogen atoms from two Schiff base ligands and one oxygen atom from an oxido ligand in the five-coordinated geometry. The geometry around the vanadium(IV) ion is a distorted square pyramidal. The V–O and V–N bond distances of the Schiff base ligand in the equatorial plane (defined by the two organic ligands), V1–O1 = 1.910(5) Å, V1–O2 = 1.898(6) Å, V1–N1 = 2.105(7) Å, V1–N2 = 2.101(7) Å, compare well with the V–O and V–N distances found in similar complexes [14, 15]. The axial V1–O3 = 1.584(6) Å is in good agreement with the V–O distances in related complexes [14, 15]. The O(3)–V(1)–N(2) angle is 85.7(2)°, while O(3)–V(1)–O(2), O(2)–V(1)–N(2), N(2)–V(1)–N(1) angles are 115.8(3), 87.1(2) and 162.2(3)°, respectively.


Corresponding author: Xiu–Jun Zheng, Department of Chemical Engineering, Harbin Institute of Petroleum, Harbin, 150027, People’s Republic of China, E-mail:

Funding source: Natural Science Foundation of Heilongjiang Province of China http://dx.doi.org/10.13039/501100005046

Award Identifier / Grant number: LH2019B029

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

  2. Research funding: The authors thank the projects of the program for the Department of Science and Technology of Natural Science Foundation of Heilongjiang Province of China (LH2019B029), https://dx.doi.org/10.13039/501100005046.

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

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Received: 2021-08-22
Accepted: 2021-09-16
Published Online: 2021-09-29
Published in Print: 2021-12-20

© 2021 Wei Wei 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. Redetermination of the crystal structure of 3-bromonitrobenzene at 200 K, C6H4BrNO2 – temperature effects on cell constants
  4. Crystal structure of (E)-ethyl 2-((4-oxo-4H-chromen-3-yl)methyleneaminooxy)acetate, C14H13NO5
  5. Crystal structure of (8R,10R,14R, Z)-2-((3–Fluoropyridin-4-yl) methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6, 6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a] phenanthren-3-one, C36H52FNO3
  6. Crystal structure of [6,6′-((1E,1′E)-(propane-1,3- diylbis(azaneylylidene))bis(methaneylylidene)) bis(3-chlorophenol)-κ4N,N′,O,O′] copper(II), C17H14Cl2CuN2O2
  7. The crystal structure of 6-amino-2-carboxypyridin-1-ium bromide, C6H7BrN2O2
  8. Redetermination of the crystal structure of bis[N,N′-ethylenebis(acetylacetoniminato)nickel(II)] sodium perchlorate, C24H36ClN4NaNi2O8
  9. The crystal structure of 3-methyl-2,6-dinitrophenol, C7H6N2O5
  10. The crystal structure of 5-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  11. Crystal structure of trans-tetraaqua-bis{2-carboxy-4-((5-carboxypyridin-3-yl)oxy)benzoato-κ1 N}cobalt(II) dihydrate C28H28O20N2Co
  12. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-(p-tolyl)furan, C23H23BrO2
  13. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(benzo[d][1,3]dioxol-5-ol ato-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV)-dichloromethane(1/1), C27H25N3O10Ti
  14. Crystal structure of (((1E,1′E)-1,2-phenylenebis(methaneylylidene))bis(hydrazin-1-yl-2-ylidene))bis(aminomethaniminium) dinitrate C10H16N10O6
  15. Crystal structure of catena-poly[triaqua-(μ 2-1,3-di(1H-imidazol-1-yl)propane-κ 2 N:N′)-(4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ 1 O)nickel(II)]N,N′-dimethylformamide (1/1), C28H35N8O8Ni
  16. The crystal structure of 3,3′-[1,4-phenylenebis(methylene)]bis(1-ethenyl-1H-imidazol-3-ium) dichloride – dichloromethane – water (1/1/1), C19H24Cl4N4O1
  17. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C13H22F12N4P2
  18. Crystal structure of dichlorido-bis(4-chlorophenyl-κC 1)tin(IV), C12H8Cl4Sn
  19. Synthesis and crystal structure of 4-acetylpyrene, C18H12O
  20. Crystal structure of 2,2′-(butane-1,4-diylbis(azanylylidene))bis(methanylylidene))bis(4-methoxyphenol), C20H24N2O4
  21. The crystal structure of (E)-2-(((5-((triphenylstannyl)thio)-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C27H21N3OS2Sn
  22. Crystal structure of diaqua-bis(μ2-6-phenylpyridine-2-carboxylate-κ3N,O:O)-bis(6-phenylpyridine-2-carboxylato-κ2N,O)lead(II) – N,N-dimethylformamide – water (1/2/4), C54H58N6O16Pb2
  23. Crystal structure of methyl 4-acetoxy-3-methoxybenzoate, C11H12O5
  24. Crystal structure of 2,2′-(propane-1,3-dilylbis(azaneylylidene))bis(methanylylidene)bis(4-methylphenol), C19H22N2O2
  25. Crystal structure of dichlorido-bis(4-methylphenyl-κC1)tin(IV), C14H14Cl2Sn
  26. Crystal structure of methyl (E)-3-(4-acetoxyphenyl)acrylate, C12H12O4
  27. The crystal structure of bis(benzoato-κ2 O,O′)-(2,9-dimethyl-1,10-phenanthroline-κ2 N,N′)-copper(II), C28H22CuN2O4
  28. Crystal structure of (8R,10R,14R,Z)-12-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one–water (2/1), C37H56NO4.5
  29. Crystal structure of dimethyl-bis(4-bromophenyl-κC1)tin(IV), C14H14Br2Sn
  30. The crystal structure of the cocrystal di-μ2-chlorido-octamethyl-di-μ3-oxido-bis(2,3,4,5-tetrafluorobenzoato-κ2 O,O′)tetratin(IV) ─ octamethyl-di-μ3-oxido-bis(μ2-2,3,4,5-tetrafluorobenzoato-κ2 O:O′)-bis(μ2-2,3,4,5-tetrafluorobenzoato-κ2 O:O;O′)tetratin(IV) C58H54Cl2F24O16Sn8
  31. Crystal structure of 3-iodo-N 2-(2-methyl-1-(methylsulfonyl)propan-2-yl)-N 1-(2-methyl-4-(perfluoropropan-2-yl)phenyl)phthalamide, C23H22F7I1N2O4S1
  32. Crystal structure of 1-(2-(4-bromophenyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)-naphthalen-2-ol – dichloromethane – dimethyl sulfoxide (1/1/1), C28H18BrNO·CH2Cl2·C2H6SO
  33. Crystal structure of [meso-5,7,7,12,14,14,-hexamethyl-1,4,8,11-tetraazacyclotetradecane]nickel(II) diperchlorate – dimethylsulphoxide (1/2), C20H48Cl2N4NiO10S2
  34. Crystal structure of 1,1′-(1,3-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S) palladium(II), C26H18N6PdS4
  35. The crystal structure of bis(6-phenylpyridine-2-carboxylato-κ2 N,O)copper(II), C24H16N2O4Cu
  36. Crystal structure of dichlorido-bis(4-chlorophenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C48H38As2Cl4O2Sn
  37. Crystal structure of (4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane-κ 8 N 2, O 6) potassium cyclopentadienide, [K([2.2.2]crypt)]Cp, C23H41KN2O6
  38. The crystal structure of bis(2-oxidopyridin-1-ium-3-carboxylato-κ2O,O′)-(phenantroline-κ2N,N′)manganese(II) - methanol (1/3), C27H28N4O9Mn
  39. Crystal structure of 4-(dimethylamino)pyridinium dibromido-tris(4-chlorophenyl-κC)stannate(IV), C25H23Br2Cl3N2Sn
  40. Crystal structure of (3E,5E)-1-(4-cyanobenzenesulfonyl)-3,5-bis(3-fluorobenzylidene)piperidin-4-one-dichloromethane (1/1), C27H20Cl2F2N2O3S
  41. Crystal structure of (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-((4-trifluoromethyl)benzenesulfonyl)piperidin-4-one, C26H18F5NO3S
  42. Crystal structure of chlorido-(4-methyl-2-((phenylimino)methyl)phenolato-κ2 N,O)-(pyridine-κ1 N)platinum(II), C19H17ClN2OPt
  43. Crystal structure of (4-methylbenzyl)(triphenyl)phosphonium chloride dihydrate, C26H28ClO2P
  44. The crystal structure of poly[μ2-chlorido-(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′silver(I)], C12H12AgClN2
  45. Crystal structure of poly[(μ4-benzene-1,2,4,5-tetracarboxylato)-bis(μ2-adipohydrazide)dicadmium], C11H15N4O6Cd
  46. The crystal structure of (E)-N′-(butan-2-ylidene)isonicotinohydrazide 0.5 hydrate C10H13N3O·0.5H2O
  47. The crystal structure of bis(6-phenylpyridine-2-carboxylate-κ2 N,O)-(2,2′-bipyridine-κ2 N,N′)zinc(II) monohydrate, C34H26N4O5Zn
  48. The crystal structure of (1R *,2S *)-1,2-bis(2-fluorophenyl)-3,8-dimethoxyacenaphthene-1,2-diol, C26H20F2O4
  49. Crystal structure of catena-poly[(μ2-1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzotriazole-κ2N:N′)-(nitrato-κ2O,O′)silver (I)], C13H15Ag1N6O3
  50. The crystal structure of [(phenantroline-κ2 N,N′)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)cobalt(II)]monohydrate, C36H26N4O5Co
  51. Crystal structure of (1E)-N-[(1E)-1-(4-chlorophenyl)ethylidene]-2-[1-(4-chlorophenyl)ethylidene]hydrazine-1-carbohydrazonamide, C 17 H 17 Cl 2 N 5
  52. The crystal structure of (E)-2-((tert-butylimino)methyl)-4-chlorophenol, C11H14ClNO
  53. Crystal structure of all-cis-2,4,6-trihydroxycyclohexane- 1,3,5-triaminium chloride sulfate, C6H18ClN3O7S
  54. Crystal structure of dichlorido-bis(dimethyl sulfoxide-κO)bis(4-methylphenyl-κC 1)tin(IV), C18H26Cl2O2S2Sn
  55. Crystal structure of dichlorido-bis(4-chlorophenyl-κC 1)(2,2′-bipyridyl-κ 2 N,N′)tin(IV), C22H16Cl4N2Sn
  56. Redetermination of the crystal structure of (E)-5-bromo-2-hydroxybenzaldehyde oxime, C 7 H 6 BrNO 2
  57. The crystal structure of (E)-amino(2-(4-methylbenzylidene)hydrazineyl)methaniminium 4-methylbenzoate, C9H13N4 + C8H7O2
  58. Crystal structure of 2-chloro-3-(isopentylamino)naphthalene-1,4-dione, C 15 H 16 ClNO 2
  59. The crystal structure of bis(2-acetyl-5-methoxyphenyl)carbonate 1.5 hydrate, C19H18O7
  60. The crystal structure of poly[(μ 4-4,4′-(azanediylbis(methylene))dibenzoato-κ 4 O:N:O′:Oʺ)zinc(II)], C16H13NO4Zn
  61. The crystal structure of catena-poly[(1,10-phenanthroline-k2N,N′)-(μ3-tetraoxidomoybdato(VI)-k3O:O′:O″)manganese(II)] C12H8N2O4MoMn
  62. Crystal structure of catena-poly[(4-hydroxyl-5-(methoylcarbonyl)thiophene-2-carboxylato-κ1 O)-(μ2-piperazine-1,4-diylbis(pyridin-4-ylmethanone)-κ2 N:N′)silver(I)] monohydrate, C23H23AgN4O8S
  63. Crystal structure of bis(4-bromo-2-(((3-bromopropyl)imino)methyl)phenolato-κ2N,O)-oxido-vanadium(IV), C20H20Br4N2O3V
  64. The crystal structure of (2a′S,2a1′S,3R,5a′S,7′R)-5-(furan-3-yl)-2a′,2a1′-dihydroxy-7′-methyldecahydro-2H-spiro[furan-3,6′-naphtho[1,8-bc]furan]-2,2′(2a′H)-dione, C19H22O7
  65. The crystal structure of 3-bromopicolinic acid, C6H4BrNO2
  66. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S,S) platinum(II), C26H18N6PtS4
  67. Synthesis and crystal structure of 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate monohydrate, C20H19NO10S
  68. The crystal structure of 3-amino-5-carboxypyridin-1-ium bromide, C6H7BrN2O2
  69. The crystal structure of (2-hydroxy-5-methyl-phenyl)-(1H-pyrazol-4-yl)-methanone hemihydrate, C11H10.5N2O2.5
  70. Crystal structure of tetraaqua-(2-(4-formylphenoxy)acetato-k1O)cadmium(II), C18H22O12Cd
  71. Crystal structure of diethyl 6,12-dimethyl-3,9-di-p-tolyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5-dicarboxylate, C32H38N2O4
  72. Crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl)ethylidene)-4-hydroxy – tetrahydrofuran (2/1), C17H16ClFN2O2.5
Heruntergeladen am 16.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2021-0340/html
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