Home Physical Sciences Crystal structure of bis ((1-((E)-((4-methoxyphenyl)imino)methyl)naphthalen-2-yl)oxy) copper(II), C36H28CuN2O4
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Crystal structure of bis ((1-((E)-((4-methoxyphenyl)imino)methyl)naphthalen-2-yl)oxy) copper(II), C36H28CuN2O4

  • Haneen Fadhil Abbas , Basil A. Saleh , Faris A. J. Al-Doghachi , Benson M. Kariuki and Gamal A. El-Hiti ORCID logo EMAIL logo
Published/Copyright: January 8, 2025
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 2

Abstract

C36H28CuN2O4, tetragonal, P4̄21c (no. 114), a = 18.9249(5) Å, c = 7.9571(5) Å, V = 2,849.9(2) Å3, Z = 4, Rgt(F) = 0.0538, wRref(F2) = 0.1336, T = 293 K.

CCDC no.: 2412752

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: Orange needle
Size: 0.29 × 0.01 × 0.01 mm
Wavelength:

μ:		 CuKα radiation (1.54184 Å)

1.44 mm−1
Diffractometer, scan mode:

θmax, completeness:		 SuperNova, ω

73.0°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 7,201, 2679, 0.081
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 1800
N(param)refined: 196
Programs: CrysAlisPRO, 1 SHELX, 2 , 3 WinGX/ORTEP 4
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.5947 (3) 0.1191 (3) 0.6115 (10) 0.0436 (16)
C2 0.6671 (3) 0.1405 (4) 0.6309 (12) 0.0495 (19)
H2 0.700116 0.108776 0.673211 0.059*
C3 0.6874 (3) 0.2062 (4) 0.5881 (11) 0.0526 (18)
H3 0.734152 0.219291 0.605449 0.063*
C4 0.6403 (3) 0.2561 (4) 0.5178 (10) 0.0489 (17)
C5 0.6637 (4) 0.3229 (4) 0.4670 (13) 0.061 (2)
H5 0.710623 0.335427 0.485207 0.073*
C6 0.6199 (4) 0.3698 (4) 0.3921 (14) 0.069 (3)
H6 0.637013 0.413248 0.355436 0.082*
C7 0.5490 (4) 0.3526 (4) 0.3703 (14) 0.072 (3)
H7 0.518103 0.385356 0.323291 0.087*
C8 0.5247 (4) 0.2874 (4) 0.4180 (12) 0.057 (2)
H8 0.477452 0.276234 0.399430 0.069*
C9 0.5682 (3) 0.2376 (3) 0.4933 (9) 0.0423 (15)
C10 0.5455 (3) 0.1661 (3) 0.5417 (10) 0.0403 (15)
C11 0.4734 (3) 0.1474 (3) 0.5255 (10) 0.0437 (17)
H11 0.443057 0.183400 0.491955 0.052*
C12 0.3686 (3) 0.0846 (3) 0.5432 (10) 0.0412 (15)
C13 0.3273 (3) 0.1328 (3) 0.6298 (12) 0.0441 (18)
H13 0.348912 0.166367 0.698076 0.053*
C14 0.2538 (3) 0.1319 (3) 0.6163 (11) 0.0470 (17)
H14 0.226798 0.165491 0.672578 0.056*
C15 0.2213 (3) 0.0812 (3) 0.5193 (11) 0.0456 (17)
C16 0.2623 (3) 0.0321 (3) 0.4323 (10) 0.0472 (18)
H16 0.240567 −0.001512 0.364734 0.057*
C17 0.3352 (3) 0.0332 (3) 0.4458 (11) 0.0458 (17)
H17 0.362019 −0.000551 0.389685 0.055*
C18 0.1062 (4) 0.1246 (5) 0.5782 (16) 0.080 (3)
H18A 0.113401 0.123166 0.697543 0.121*
H18B 0.057574 0.114595 0.553427 0.121*
H18C 0.118132 0.170668 0.536531 0.121*
N2 0.4441 (2) 0.0860 (3) 0.5516 (8) 0.0400 (13)
O1 0.5797 (2) 0.0554 (2) 0.6580 (7) 0.0493 (12)
O2 0.1498 (2) 0.0734 (3) 0.5000 (9) 0.0616 (16)
Cu1 0.500000 0.000000 0.60260 (16) 0.0420 (3)

1 Source of material

In a three-neck round-bottom flask fitted with a thermometer and condenser, a solution of (E)-1-(((4-methoxyphenyl)imino)methyl)naphthalene-2-ol (0.28 g, 1.0 mmol) in dry EtOH (20 mL) was stirred. The solution was heated under reflux while a solution of NaOH (10 % w/v) was added dropwise. Subsequently, a solution of copper nitrate trihydrate (0.24 g, 1.0 mmol) in EtOH (10 mL) was added dropwise. The mixture was maintained under reflux for 5 h, and the progress of the reaction was monitored using thin-layer chromatography. The mixture was allowed to cool, and the solid produced was collected by filtration, washed with EtOH (3 × 10 mL), and dried in a vacuum oven to give the title compound in 82 % yield as orange crystals, mp 340–341 °C. IR (KBr; cm−1): 1607 (C=N), 1501 (C=C), 3017 (C–H).

2 Experimental details

All hydrogen atoms were identified by difference Fourier syntheses. The methyl group was refined with idealized geometry as a rigid group and allowed to rotate about the O–C bond (AFIX 137 option of the SHELXL program 3 ). The Uiso values of the hydrogen atoms of methyl groups were set to 1.5 Ueq (C) and the Uiso values of all other hydrogen atoms were set to 1.2 Ueq (C, N).

3 Comment

Schiff bases are cost-effective, easily synthesized, and environmentally friendly compounds used as ligands in various applications, including the development of new anti-corrosion agents. 5 , 6 , 7 Schiff bases of 2-hydroxynaphthaldehyde act as multidentate ligands with important potential applications. 8 The strong chelation affinity of these Schiff bases for transition metals can be used to produce useful complexes. 9 , 10 , 11 Copper complexes containing O and N donor systems show interesting biological activities. 12 The synthesis of such complexes is therefore of wide interest.

The asymmetric unit of the crystal structure of the title compound consists of one [(4-methoxyphenyl)imino]-methylnaphthalenolate ligand and a Cu ion located on a 2-fold rotation axis (Figure). The ligand has two planar fragments, namely (iminomethyl)naphthalen-2-olate (C1–C11, N2, O1) and 4-methoxyaniline (C12–C18, O2) groups. The twist angle between the planes of the two fragments of one ligand is 58.8 (1)°.

The Cu ion is coordinated by two nitrogen and two oxygen atoms in trans geometry. Atoms O1, Cu1 and N2 form a triangle and a second triangle is generated by twofold rotation to complete the Cu coordination. The twist angle between the planes through the triangles is 35.8 (1)°, leading to distortion from perfect planarity. Similar distortion is also observed in, for example, bis(N-menthyl-2-amino-5,5,5-trifluoro-4-trifluoromethyl-4-hydroxy-pentane–N, O)-copper(II) 13 with an angle of 14.77° and in bis(N-(5,5,5-trifluoro-4-trifluoromethylpentan-2-yl-4-olato)methylamine)-copper(II) 14 with an angle of 33.34°.

In the crystal structure, complex units related by glide symmetry are stacked along the c axis. In a stack, the distance between the copper ions of neighbouring complex units is 3.979 Å. Adjacent stacks are linked by C–H⋯O contacts with a C18⋯O2 distance of 3.49(1) Å and a C18–H18B⋯O2 angle of 153.7°. Bond lengths and angles are all in the expected ranges. 15

Corresponding author: Gamal A. El-Hiti, Department of Optometry, College of Applied Medical Sciences, King Saud University, Riyadh 11433, Saudi Arabia, E-mail:

Funding source: King Saud University, Riyadh, Saudi Arabia

Award Identifier / Grant number: RSP2024R404

Acknowledgments

The authors are grateful to the University of Basrah for its support. G. A. El–Hiti acknowledges the support received from the Researchers Supporting Project (number RSP2024R404), King Saud University, Riyadh, Saudi Arabia.

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

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

  3. Research funding: University of Basrah, Researchers Supporting Project (number RSP2024R404), King Saud University, Riyadh, Saudi Arabia.

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Received: 2024-11-19
Accepted: 2024-12-24
Published Online: 2025-01-08
Published in Print: 2025-04-28

© 2024 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-2024-0449
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2
  4. Synthesis and crystal structure of ethyl (2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR,E)-10-(((3,4-dichlorobenzyl)oxy)imino)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate
  5. The crystal structure of pyrazole nitrate
  6. Crystal structure of tetramethyl-bis(μ2-2-(2-hydroxy-3-methoxybenzylidene)-1-(6-(2-(2-hydroxy-3-methoxybenzylidene)hydrazine-1-carbonyl)picolinoyl)hydrazin-1-ido-κ4O,N,O′:O′)ditin(II) ─ ethanol (1/2), C54H62N10O14Sn2
  7. Crystal structure of catena-poly[μ3-iodido-(4-bromopyridine-κ1N)copper(I)], C5H4BrNCuI
  8. The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P
  9. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(phenylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C34H48N2O
  10. The crystal structure of (E)-3-((E)-3-(4-ethoxy-3-methoxyphenyl)-1-hydroxyallylidene) chroman-2,4-dione, C21H18O6
  11. The crystal structure of trans–L/D-[bis-(2-methyl-8-hydroxyquinoline-κ2 N,O) bis-(1,3,5-triaza-7-phosphaadamantane-κ2 P)cobalt(III)] tetrafluoroborate
  12. Crystal structure of 9-chloro-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C14H15ClN4
  13. Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3
  14. The crystal structure of 4–bromo-3,5-dinitropyrazole
  15. Crystal structure of 8-hydroxy-3,5,8a-trimethyl-7,8,8a,9-tetrahydronaphtho[2,3-b]furan-4,6-dione, C15H16O4
  16. Crystal structure of 5-hydroxy-3,5,8a-trimethyl-4a,5,6,7,8a,9-hexahydronaphtho[2,3-b]furan-4,8-dione, C15H18O4
  17. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(p-tolylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C35H50N2O
  18. The crystal structure of catena-poly((μ2-1,3,5-tri(1H- imidazol-1-yl)benzene κ2N:N′)-bis(4-hydroxbenzoato-κ1O)-zinc(II) monohydrate), C29H24N6O7Zn
  19. Crystal structure of 2-(benzo[d]oxazol-2-yl)acetonitrile, C9H6N2O
  20. Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7
  21. The crystal structure of the double salt potassium 1-methylpiperazine-1,4-di-ium trinitrate, C5H14KN5O9
  22. Crystal structure of 5′-hydroxy-6′-methoxy-1′-methyl-2′,3′,8′,8a′-tetrahydro-1′H-spiro[cyclohexane-1,7′-cyclopenta[ij]isoquinoline]-2,5-dien-4-one, C18H19NO3
  23. The crystal structure of 1,1′-(2,3,5,6-tetramethylpyrazine-1,4-diyl)bis(ethan-1-one), C12H18N2O2
  24. Crystal structure of [μ2-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ2O:O′)] bis(μ2-4,4′-trimethylenedipyridyl-κ2N:N′)disilver(I), C18H24AgN3O4S
  25. Crystal structure of bis ((1-((E)-((4-methoxyphenyl)imino)methyl)naphthalen-2-yl)oxy) copper(II), C36H28CuN2O4
  26. Synthesis and crystal structure of 6,6′-((1E,11E)-5,8-dioxa-2,11-diazadodeca-1,11-diene-1,12-diyl) bis(2,4-di-tert-butylphenol), C36H56N2O4
  27. The crystal structure of barium hexahydroxidoiridate(IV) dihydroxide, Ba2[Ir(OH)6](OH)2
  28. Crystal structure of cinnamoyl ferrocene, C19H16FeO
  29. Crystal structure of (E)-3-(4-butoxyphenyl)acryloylferrocene, C23H24FeO2
  30. Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
  31. The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5
  32. The crystal structure of 1,3,5-trichloro-2-nitrobenzene
  33. The crystal structure of tris(μ2-bromido)-bis(η6-p-cymene)-diosmium(II) tetrafluoroborate, C20H28BBr3F4Os2
  34. Crystal structure of new barium lithium manganese fluorides: Ba14Li1.87Mn14.13F68 with a Jarlite–related structure
  35. Crystal structure of (4-fluorobenzyl)triphenylphosphonium chloride, C25H21ClFP
  36. The crystal structure of calcitriol–chloroform (1/1), C27H44O3⋅CHCl3
  37. The crystal structure of (E)-1-((3)-nitrophenyl)pyren-3-(pyren-1-yl)prop-2-en-1-one, C25H15NO3
  38. Crystal structure of (E)-2-hydroxy-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H16N2O3
  39. Crystal structure of (E)-(3-(thiophen-2-yl)acryloyl)ferrocene, C17H14FeOS
  40. Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2
  41. Synthesis and crystal structure poly[diaqua(μ3-3-(((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl) methyl)ammonio)propanoate-κ3 O:O′:O″) sodium(I)] monohydrate, C20H24NNaO12S
  42. Crystal structure of 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine C19H18N4O2
  43. Synthesis and crystal structure of 4-(difluoromethyl)-1-methyl-N-(pyridin-3-yl)-1H-pyrazole-3-carboxamide hydrate, C11H12F2N4O2
  44. The crystal structure of caesalfurfuric acid B, C22H32O4
  45. The crystal structure of 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone, C12H9Br2N3O3
  46. The crystal structure of bis{chlorido-[μ2-(1-oxidopyridin-2-yl)(pyridin-2-yl)amido-κ3 O,N, N′]copper(II)}, C20H16Cl2Cu2N6O2
  47. The crystal structure of 3-amino-2-formyl-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile, C22H16N2O
  48. The crystal structure of 1,1′-(2,5-dimethylpyrazine-1,4-diyl)bis(ethan-1-one), C10H14N2O2
  49. Crystal structure of 5′-(9-phenyl-9H-carbazol-3-yl)-[2,2′-bithiophene]-5-carbaldehyde, C27H17NOS2
  50. The crystal structure of the double salt dipyridin-1-ium bromide tribromide
  51. Crystal structure of (E)-(3-(3-methylthiophen-2-yl)acryloyl)ferrocene, C18H16FeOS
  52. Crystal structure of (E)-(3-(4-phenoxyphenyl)acryloyl)ferrocene, C25H20FeO2
  53. Crystal structure of (E)-(3-(3,4-dimethylphenyl)acryloyl)ferrocene, C21H20FeO
  54. Crystal structure of [(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N‴)tetracyanidodiplatinum(II)] dimethyl sulfoxide solvate, C18H36N8O2Pt2S2
  55. Crystal structure of (4-ethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO2P
  56. Crystal structure of (1-naphthalen-1-yl-methyl)triphenylphosphonium chloride ethanol solvate, C31H30ClOP
  57. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)platinum(II) bis[tribromido(dimethyl sulfoxide-κS)platinate(II)], C14H36Br6N4O2Pt3S2
  58. Crystal structure of (2-methylbenzyl)triphenylphosphonium chloride ethanol solvate, C28H30ClOP
  59. Crystal structure of bis(η2, σ1-8-methoxycyclooct-4-enyl)(μ2-1,4,8,11-tetraazacyclotetradecane-κ4 N, N′, N″, N‴)diplatinum(II) dibromide, C28H54Br2N4O2Pt2
  60. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetrabromidopalladate(II), C10H24Br4N4Pd2
  61. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) bis[trichlorido(dimethyl sulfoxide-κS)platinate(II)], C14H36Cl6N4O2PdPt2S2
  62. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetraiodidopalladate(II), C10H24I4N4Pd2
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