Startseite Crystal structure of (((3-nitrophenyl)sulfonyl)-β-alaninato-κO)bis(2,2′-bipyridine-κ 2 N, N′)copper(II) 3-nitrobenzenesulfonate, C35H29CuN7O11S2
Artikel Open Access

Crystal structure of (((3-nitrophenyl)sulfonyl)-β-alaninato-κO)bis(2,2′-bipyridine-κ 2 N, N′)copper(II) 3-nitrobenzenesulfonate, C35H29CuN7O11S2

  • Zheng-Jun Liu ORCID logo EMAIL logo , Xiao-Miao Chen ORCID logo , Qiang Wu , Wu-Chao Zhou , Xu-Min Jiao und Juan Tan
Veröffentlicht/Copyright: 23. Oktober 2024

Abstract

C35H29CuN7O11S2, triclinic, P 1 (no. 2), a = 12.2643(9) Å, b = 13.3486(9) Å, c = 13.5247(11) Å, α = 69.595(7)°, β = 71.363(7)°, γ = 67.275(7)°, V = 1869.8(3) Å3, Z = 2, R gt(F) = 0.0570, wR ref(F 2) = 0.1781, T = 293(2) K.

CCDC no.: 1881202

A part of 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: Blue block
Size: 0.68 × 0.36 × 0.34 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 0.77 mm−1
Diffractometer, scan mode: Multiwire proportional, φ and ω
θ max, completeness: 29.4°, >99 %
N(hkl)measured, N(hkl)unique, R int: 17121, 8714, 0.028
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 5,797
N(param)refined: 508
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
Cu1 0.75955 (3) 0.73506 (3) 0.54720 (3) 0.04072 (15)
S1 0.48513 (8) 0.44550 (8) 0.72757 (7) 0.0466 (2)
O1 0.5261 (8) 0.0130 (4) 1.1074 (4) 0.185 (3)
O2 0.6698 (7) 0.0551 (5) 0.9786 (7) 0.180 (4)
O8 0.3993 (2) 0.4928 (3) 0.6607 (2) 0.0670 (8)
O9 0.6089 (2) 0.3940 (2) 0.6827 (2) 0.0598 (7)
O10 0.6117 (3) 0.7882 (2) 0.7380 (2) 0.0642 (7)
O11 0.6981 (2) 0.63453 (19) 0.67902 (18) 0.0444 (6)
N1 0.5620 (9) 0.0747 (5) 1.0257 (6) 0.127 (3)
N2 0.4797 (3) 0.5433 (3) 0.7741 (2) 0.0457 (7)
N4 0.6166 (2) 0.7801 (2) 0.4854 (2) 0.0424 (6)
N5 0.7470 (3) 0.9019 (2) 0.4710 (2) 0.0486 (7)
N6 0.8848 (2) 0.6654 (2) 0.4168 (2) 0.0441 (7)
N7 0.9163 (3) 0.6938 (2) 0.5877 (2) 0.0448 (7)
C1 0.5190 (5) 0.2492 (4) 0.8855 (4) 0.0670 (12)
H1 0.601483 0.234490 0.855770 0.080*
C2 0.4762 (7) 0.1772 (4) 0.9760 (5) 0.0915 (19)
C3 0.3539 (9) 0.1967 (6) 1.0224 (5) 0.115 (3)
H3 0.327059 0.145885 1.083971 0.138*
C4 0.2753 (7) 0.2909 (7) 0.9762 (6) 0.117 (2)
H4 0.192975 0.305074 1.006645 0.140*
H2 0.404 (6) 0.582 (6) 0.792 (5) 0.140*
C5 0.3130 (4) 0.3665 (4) 0.8854 (4) 0.0785 (14)
H5 0.257154 0.431663 0.854900 0.094*
C6 0.4356 (4) 0.3446 (3) 0.8397 (3) 0.0543 (9)
C7 0.5619 (3) 0.5143 (3) 0.8468 (3) 0.0473 (8)
H7A 0.641606 0.467946 0.818778 0.057*
H7B 0.531100 0.472014 0.917996 0.057*
C8 0.5703 (4) 0.6204 (3) 0.8544 (3) 0.0529 (9)
H8A 0.616000 0.601223 0.908764 0.063*
H8B 0.489340 0.667259 0.878847 0.063*
C9 0.6291 (3) 0.6885 (3) 0.7498 (3) 0.0420 (8)
C16 0.5565 (3) 0.7105 (4) 0.4972 (3) 0.0537 (9)
H16 0.575440 0.639097 0.543988 0.064*
C17 0.4668 (4) 0.7427 (5) 0.4413 (4) 0.0722 (14)
H17 0.426757 0.693076 0.448340 0.087*
C18 0.4379 (4) 0.8503 (5) 0.3746 (4) 0.0822 (16)
H18 0.376695 0.874204 0.337305 0.099*
C19 0.4984 (4) 0.9211 (5) 0.3634 (3) 0.0709 (13)
H19 0.479265 0.993342 0.318145 0.085*
C20 0.5884 (3) 0.8854 (3) 0.4195 (3) 0.0506 (9)
C21 0.6595 (3) 0.9542 (3) 0.4145 (3) 0.0508 (9)
C22 0.6398 (5) 1.0663 (4) 0.3555 (3) 0.0730 (14)
H22 0.579670 1.102144 0.315675 0.088*
C23 0.7127 (6) 1.1225 (4) 0.3582 (4) 0.0916 (19)
H23 0.701026 1.197542 0.320260 0.110*
C24 0.8001 (5) 1.0696 (4) 0.4151 (5) 0.0868 (17)
H24 0.849610 1.106955 0.416380 0.104*
C25 0.8149 (4) 0.9585 (4) 0.4717 (4) 0.0677 (12)
H25 0.874785 0.921995 0.511871 0.081*
C26 0.8626 (4) 0.6534 (4) 0.3324 (3) 0.0576 (10)
H26 0.782372 0.671308 0.329256 0.069*
C27 0.9522 (4) 0.6159 (4) 0.2490 (3) 0.0648 (11)
H27 0.933401 0.607934 0.191256 0.078*
C28 1.0703 (4) 0.5907 (4) 0.2547 (4) 0.0681 (12)
H28 1.133175 0.565856 0.199700 0.082*
C29 1.0953 (3) 0.6020 (3) 0.3406 (3) 0.0582 (10)
H29 1.175059 0.583848 0.345148 0.070*
C30 1.0010 (3) 0.6407 (3) 0.4211 (3) 0.0430 (8)
C31 1.0183 (3) 0.6564 (3) 0.5168 (3) 0.0455 (8)
C32 1.1310 (3) 0.6335 (4) 0.5367 (4) 0.0663 (12)
H32 1.201320 0.609983 0.486838 0.080*
C33 1.1369 (4) 0.6462 (4) 0.6315 (5) 0.0794 (15)
H33 1.211584 0.631119 0.646165 0.095*
C34 1.0331 (4) 0.6807 (4) 0.7038 (5) 0.0769 (14)
H34 1.036391 0.687901 0.768673 0.092*
C35 0.9236 (4) 0.7049 (4) 0.6800 (4) 0.0598 (10)
H35 0.852748 0.729566 0.728982 0.072*
S2 0.16580 (9) 0.69617 (9) 0.93808 (8) 0.0590 (3)
O3 −0.1695 (6) 0.9855 (5) 0.7352 (6) 0.170 (3)
O4 −0.1665 (5) 1.1528 (4) 0.7106 (6) 0.172 (3)
O5 0.0617 (3) 0.6572 (3) 0.9878 (3) 0.0928 (11)
O6 0.2433 (4) 0.6721 (3) 1.0076 (3) 0.1040 (13)
O7 0.2293 (2) 0.6640 (2) 0.8381 (2) 0.0656 (8)
N3 −0.1312 (5) 1.0508 (5) 0.7459 (5) 0.1149 (19)
C10 0.1539 (4) 0.9160 (5) 0.9087 (4) 0.0722 (13)
H10 0.218702 0.885615 0.942951 0.087*
C11 0.1092 (5) 1.0302 (5) 0.8710 (5) 0.0888 (16)
H11 0.143064 1.076719 0.880609 0.107*
C12 0.0154 (5) 1.0759 (4) 0.8194 (5) 0.0849 (15)
H12 −0.014609 1.153344 0.792551 0.102*
C13 −0.0340 (4) 1.0049 (4) 0.8078 (4) 0.0684 (12)
C14 0.0080 (3) 0.8911 (3) 0.8462 (3) 0.0572 (10)
H14 −0.027630 0.844877 0.838393 0.069*
C15 0.1041 (3) 0.8458 (3) 0.8966 (3) 0.0513 (9)

1 Source of material

β-Alanine (8.91 g, 100 mmol) and sodium hydroxide (8.00 g, 200 mmol) were dissolved in 100 mL of deionized water. Subsequently, m-nitrobenzenesulfonyl chloride (22.16 g, 100 mmol) was introduced into the reaction mixture at ambient temperature under constant stirring. After a reaction period of 10 h, the pH of the solution was carefully adjusted to 1 using a 6 mol/L hydrochloric acid solution. The resultant precipitate was then separated by filtration and subsequently dried to obtain a white solid product. Next, mix 316.9 mg of the aforementioned white solid with Cu(CH3COO)2⋅H2O (99.82 mg, 0.5 mmol) and 2,2′-bipyridine (78.09 mg, 0.5 mmol), and dissolve them in 18 mL of a 1:1 methanol-water solution. Then, adjust the pH of the solution to approximately 7 using a 2 mol/L sodium hydroxide solution. Load the solution into a Teflon-lined reaction vessel and react at 80 °C for 12 h and then filter. Blue block crystals of the title compound were obtained by slow evaporation at room temperature within one week.

2 Experimental details

Hydrogen atoms were added using riding models. Their U iso values were set to 1.2U eq of the parent atoms. The structure was solved with the ShelXT 3 structure solution program and refined with the ShelXL. 4

3 Comment

Sulfonated amino acids are a class of amino acid derivatives formed by the substitution of a sulfonate group on the nitrogen atom of the amino group. These compounds have shown a broad potential for application in the fields of biochemistry and materials science due to their unique chemical properties. 5 , 6 , 7 , 8 Sulfonated amino acids can participate in coordination not only through the oxygen atom and the nitrogen atom of their amino acid group but also the oxygen atoms of their sulfonate group can form coordination bonds with metal ions. 9 , 10 , 11 This dual coordination capability makes sulfonated amino acids ideal candidates for constructing new metal complexes. These complexes may exhibit a variety of coordination geometries. In our group, a series of sulfonylated amino acid complexes have been successfully synthesized. 12 , 13 , 14 , 15 This contribution is part of our ongoing research focus on the complexes of sulfonylated amino acids.

In this paper, the synthesis and crystal structure of a new copper(II) complex with ((3-nitrophenyl)sulfonyl)-β-alanine and 2,2′-bipyridine were reported. Single crystal X-ray structure analysis reveals that the title complex crystallizes in the triclinic system with space group P 1 . The asymmetric unit is composed of an independent Cu(II) ion, one ((3-nitrophenyl)sulfonyl)-β-alanine ligand, two 2,2′-bipyridine ligands, and one 3-nitrobenzenesulfonate. The crystallographically unique Cu(II) ion of the title complex is five-coordinated by four N atoms (N4, N5, N6, N7) from two 2,2′-bipyridine groups, one O atom (O11) from ((3-nitrophenyl)sulfonyl)-β-alanine group, giving rise to a hexahedral geometry. Cu–N bond lengths fall in the range 1.977(3)–2.155(3) Å, and Cu–O bond length is 1.950(2) Å. The bond lengths observed fall within the expected range and align closely with those documented for analogous complexes in prior studies. 12 , 13 , 16 The extended three-dimensional supramolecular network is constructed through hydrogen bond N2–H2⋯O7, and ππ interactions between the aromatic rings of 3-nitrobenzenesulfonate and 2,2′-bipyridine.


Corresponding author: Zheng-Jun Liu, Key Laboratory of Agricultural Resources and Environment in High Education Institute of Guizhou Province, Anshun University, Anshun, 561000, P.R. China, E-mail:

Award Identifier / Grant number: asxybsjj202314

Award Identifier / Grant number: Qianjiaoji[2023]025

Award Identifier / Grant number: Qianjiaoji[2023]086

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

  2. Research funding: Doctoral Fund of Anshun University (asxybsjj202314), Key Laboratory of Agricultural Resources and Environment in High Education Institute of Guizhou Province (Qianjiaoji[2023]025), and Porous Materials and Green Catalysis Innovation Team in High Education Institute of Guizhou Province (Qianjiaoji[2023]086).

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

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Received: 2024-08-09
Accepted: 2024-10-10
Published Online: 2024-10-23
Published in Print: 2024-12-17

© 2024 the author(s), 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
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  5. Crystal structure of poly[bis(μ3-3-fluoro-4-(1H-1,2,4-triazol-1-yl)benzoato-κ3 O:O′:N)cadmium(II)] – dimethylformamide (1/1), C21H17CdF2N7O5
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  8. Crystal structure of 2-chloro-4-fluorobenzyl (R)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18ClFO3
  9. Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid]-(methylsulfinyl)methane, C15H16N2O6S
  10. The crystal structure of 2-ethyl-1,1-dimethyl-1H-benzo[e]indole, C16H17N
  11. The crystal structure of (Z)-5-amino-N -hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  12. The crystal structure of 2,2,5-trimethyl-3-(4-(4-(5-phenyl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)phenyl)imidazolidin-4-one, C24H24N4O2S
  13. The crystal structure of tetrakis(μ2-acetato-κ2 O:O′)-bis[(4′-phenyl-4,2′:6′,4″-terpyridine-κ1 N)dicopper(II)], C25H21CuN3O4
  14. Crystal structure of poly(3-thiophenecarboxylato-κ 3 O,O′:O′)-(methanol-κO)cadmium(II), C11H10O5S2Cd
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  17. Crystal structure of 1,1′,1″-(nitrilotris(ethane-2,1-diyl))tris(3-(4-(((E)-pyridin-2-ylmethylene)amino)phenyl)urea), C45H47N13O4
  18. Crystal structure of a (E)-4-bromo-N-(4-(diethylamino)-2-hydroxybenzylidene) benzenaminium acetate ─ 4-bromoaniline (1/1)
  19. Crystal structure of 2,2′-(iminobis(methylene))bis(benzimidazolium) bis(p-toluenesulfonate), C30H31N5O6S2
  20. The crystal structure of alogliptinium meta-chlorobenzoate
  21. Crystal structure of 4-bromobenzyl 2-(6-methoxy-naphthalen-2-yl)propanoate, C21H19BrO3
  22. The hydrated double salt structure of (E)-4-(2-benzylidenehydrazine-1-carbonyl)pyridin-1-ium cation with 2-hydroxybenzoate and benzoate anions
  23. Crystal structure of (R)(R)-5-chloro-3-((S,1E,3E)-3,5-dimethyl-hepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-2,6,7,8-tetrahydroisoquinolin-7-yl acetate, C21H24ClNO4
  24. The crystal structure of bis(3-oxo-1,3-diphenylprop-1-en-1-olato-κ 2 O:O′)-bis(1,4-dioxane-κ 1 O)nickel(II), C38H38O8Ni
  25. Crystal structure of poly[aqua-(pyridine-3-carboxylato-κ1 N)(pyridine-3-carboxylato-κ2 O,O′) cadmium(II)] dihydrate, C12H14N2O7Cd
  26. The crystal structure of 4-(4-phenyl-5-(((1-(2,4,6-tribromophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-4H-1,2,4-triazol-3-yl)pyridine, C22H14Br3N7S
  27. The crystal structure of N-benzylquinoline-2-carbothioamide, C17H14N2S
  28. Crystal structure of bis(3-isopropylphenyl)-4,4′-bipyridinium dichloride dihydrate, C28H30N2⋅2Cl⋅2H2O
  29. The crystal structure of ethyl 2-amino-4-(cyanophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C19H18N2O4
  30. Crystal structure of (4R,10S)-6-hydroxy-7-isopropyl-4,10-dimethyl-1,2,3,5-hexahydro-6,10-epoxyazulen-9-one, C15H22O3
  31. The crystal structure of (E)-(2-(2-hydroxy-3-methoxybenzylidene)aminophenyl)arsonic acid, C14H14AsNO5
  32. The crystal structure of poly[(μ 2-2-aminoisophthalato-κ4O,O′:O″:O″′)-(N-methylpyrrolidone κ1O)-dioxido-uranium(VI)], C13H14N2O7U
  33. The crystal structure of the co-crystal isonicotinamide · terephthalic acid, C8H6O4·2(C6H6N2O)
  34. The crystal structure of (E)-1-phenyl-3-(p-tolylthio)but-2-en-1-one, C17H16OS
  35. The crystal structure of 4,5-bis((Z)-chloro(hydroxyimino)methyl)-1H-imidazol-3-ium chloride monohydrate
  36. The crystal structure of 1,2-bis(4-(dimethylamino)phenyl)ethane-1,2-dione. C18H20N2O2
  37. Crystal structure of 2-chloro-4-fluorobenzyl 2-acetoxybenzoate, C16H12ClFO4
  38. Crystal structure of methyl 1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate, C19H14N2O2
  39. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl)(5-fluoro-2-iodophenyl)methanone, C19H17FINO4
  40. Crystal structure of tetrachlorido-bis(1-[(1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2 N:N′)dicopper, C36H32Cu2N24Cl4
  41. Crystal structure of 2-(2,3-bis(4-methoxyphenyl)-1H-pyrrolo[2,3-b]quinoxalin-1-yl)anilin, C30H24N4O2
  42. Crystal structure of 5,7-dihydroxy-2-phenyl-4H-chromen-4-one–N,N-dimethylformamide(1/1), C18H17NO5
  43. The crystal structure of bis(μ 2-biphenyl-2,2′-dicarboxylato)-diaqua-bis(nitrato)-bis(2,2′:6′,2′′-terpyridine)dineodymium(III), C46H32I2N8Nd2O16
  44. Crystal structure of (Z)-4-amino-N -((4-chlorophenyl)(phenyl)methylene)benzohydrazide, C20H16ClN3O
  45. Crystal structure of (E)-6,8-dimethoxy-4-(4-morpholinobenzylidene)-3,4-dihydro-1-benzoxepin-5(2H)-one, C23H25NO5
  46. Crystal structure of (R)-2-((3-(3-aminopiperidin-1-yl)-6-methyl-5-oxo-1,2,4-triazin-4(5H)-yl) methyl)-4-fluorobenzonitrile benzoate monohydrate, C24H27FN6O4
  47. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylato-κ 3 N,O,O)copper(II)]monohydrate, C12H15NO9Cu
  48. Crystal structure of (((4-chlorophenyl)sulfonyl)glycinato-κ 2 N,O)bis(1,10-phenanthroline-κ 2 N,N′)cobalt(II) tetrahydrate, C32H30ClCoN5O8S
  49. Crystal structure of (((3-nitrophenyl)sulfonyl)-β-alaninato-κO)bis(2,2′-bipyridine-κ 2 N, N′)copper(II) 3-nitrobenzenesulfonate, C35H29CuN7O11S2
  50. Crystal structure of 3-phenoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C27H24O4
  51. 6-(2′,3′-Dihydroxy-3′-methylbutyl)-7-methoxy-8-(3″-methylbut-2″-en-1″-yl)-2H-chromen-2-one, C20H26O5
  52. Crystal structure of bromido-(2,2′:6′,2″-terpyridine-4′-onato-κ3N)palladium(II) methanol solvate
  53. The crystal structure of ethyl 2-amino-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H22N2O6
  54. Crystal structure of (1E,3E,5E)-1,6-bis(4-(pentyloxy)phenyl)hexa-1,3,5-triene, C28H36O2
  55. The crystal structure of tris(2-bromo-4-methylphenyl)amine, C21H18Br3N
  56. The crystal structure of 3-(2,5-dimethylanilino)-1-(2,5-dimethylphenyl)-4-methyl-1H-pyrrole-2,5-dione, C21H22N2O2
  57. Crystal structure of dicarbonyl (μ2-indole-2-carboxylato κ2 O:O′)tris(triphenylarsine-κAs)dirhodium(I) acetone solvate, C68H56As3NO5Rh2
  58. The crystal structure of 4-chloro-2-formylphenyl 4-methylbenzenesulfonate, C14H11ClO4S
  59. Crystal structure of 4-iodobenzyl 2-(6-methoxynaphthalen-2-yl) propanoate, C21H19IO3
Heruntergeladen am 2.10.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2024-0334/html?srsltid=AfmBOoo9dbT8iO4OEbFqbtPIJM7cJ27SNsZ5oDEBzzfXaaajFAg79igk
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