Home Crystal structure of the coordination polymer catena-poly[chlorido-{μ2-2-(((3,5-dimethyl-1H-pyrazol-1-yl)methyl)amino)-3-hydroxybutanoato-κ4N,N,O:O′}copper(II)], C11H16ClCuN2O3
Article Open Access

Crystal structure of the coordination polymer catena-poly[chlorido-{μ2-2-(((3,5-dimethyl-1H-pyrazol-1-yl)methyl)amino)-3-hydroxybutanoato-κ4N,N,O:O′}copper(II)], C11H16ClCuN2O3

  • Mouslim Messali EMAIL logo , Rafika El Ati , Rachid Touzani , Mohamed Reda Aouad and Ismail Warad EMAIL logo
Published/Copyright: March 10, 2018

Abstract

C11H16ClCuN2O3, monoclinic, P21/n (no. 14), a = 5.6017(4) Å, b = 10.7601(8) Å, c = 10.4036(8) Å, β = 95.697(2)°, V = 623.98(8) Å3, Z = 2, Rgt(F) = 0.0321, wRref(F2) = 0.0833, T = 100(1) K.

CCDC no.: 1824676

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Blue block
Size:0.07 × 0.05 × 0.02 mm
Wavelength:Cu radiation (1.54178 Å)
μ:4.5 mm−1
Diffractometer, scan mode:Bruker X8 PROSPECTOR APEX2, φ and ω-scans
θmax, completeness:66.9°, >99%
N(hkl)measured, N(hkl)unique, Rint:14015, 2145, 0.027
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2141
N(param)refined:169
Programs:Bruker programs [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
Cu10.10252(8)0.39832(5)0.65832(5)0.0288(2)
Cl1−0.20257(16)0.27451(9)0.69674(9)0.0323(2)
O10.1517(5)0.3154(3)0.4961(3)0.0322(6)
O20.2738(6)0.3585(3)0.3046(3)0.0375(7)
O30.8352(5)0.5510(3)0.5388(3)0.0313(6)
H30.847(10)0.6267(19)0.523(6)0.047*
N10.4025(6)0.4881(3)0.6216(3)0.0294(7)
H10.54310.43860.65990.035*
N30.1435(6)0.4966(3)0.8214(3)0.0303(7)
C10.2687(7)0.3812(4)0.4195(4)0.0308(8)
C20.4129(7)0.4932(4)0.4798(3)0.0295(8)
H20.33440.57180.44600.035*
C30.6749(7)0.4901(4)0.4421(4)0.0301(8)
H3A0.72500.40110.43850.036*
C40.6950(7)0.5469(4)0.3101(4)0.0357(9)
H4A0.63740.63290.30930.054*
H4B0.59760.49870.24430.054*
H4C0.86300.54560.29140.054*
C50.4052(7)0.6076(4)0.6885(4)0.0337(9)
H5A0.29590.66730.64000.040*
H5B0.56910.64310.69790.040*
N20.3241(6)0.5817(4)0.8155(3)0.0315(7)
C70.3881(7)0.6325(4)0.9323(4)0.0305(8)
C80.2436(7)0.5786(4)1.0170(4)0.0312(8)
H80.24540.59531.10670.037*
C90.0940(7)0.4946(4)0.9446(4)0.0299(8)
C100.5825(7)0.7263(4)0.9557(4)0.0353(9)
H10A0.73300.69150.93100.053*
H10B0.60200.74841.04750.053*
H10C0.54060.80070.90400.053*
C11−0.0910(7)0.4130(5)0.9927(4)0.0351(9)
H11A−0.24860.45260.97660.053*
H11B−0.05370.39951.08570.053*
H11C−0.09290.33300.94760.053*

Source of material

Preparation of the copper(II) complex: 2-(((3,5-dimethyl-2H-pyrrol-2-yl)methyl)amino)-3-hydroxybutanoic acid (0.335 g, 1 mmol) in 20 mL of EtOH was added to CuCl2⋅2H2O (0.17 g, 1 mmol) dissolved in 10 mL of EtOH. The reaction mixture was left at room temperature for couple of days until the complete evaporation of solvent. The blue powder was washed several times with THF. Suitable crystals were obtained by recrystallization from a mixture of Ether/EtOH. A blue crystal was obtained with a period of 6 days. Yield (22%).

Experimental details

Hydrogen atoms were placed at the calculated positions and refined using a riding model with Uiso(H) = 1.2Ueq or 1.5Ueq of the adjacent non-hydrogen atom. H3 atom position was localized from the difference map and refined with the DFIX option N—H = 0.87 Å and Uiso(H) = 1.5Ueq(O3).

Discussion

Amino acids can bind transition metal like other chelate ligands in monodentate, bidentate and tridentate modes [3, 4] . The coordination of metals with amino acids especially with copper has been the subject of many studies because they are simple systems that can serve as a model for metallo-proteins [5]. Amino acids-metal complexes have been used as antibacterial and anticancer drugs [2], [3], [4], [5], [6], [7]. The research area of coordination polymers was established by Robson and Hoskins about 30 years ago [8]. Design and synthesis of coordination polymers have attracted interests for their unprecedented and possibly useful physical properties [6], [7], [8], [9], [10].

Each Cu(II) atom in the synthesized coordination polymers is coordinated by five donor atoms: one Cl, two O and two N atoms. The apical position of copper center was occupied by O3 atom from the hydroxyl group. A Jahn-Teller effect of the Cu(II) ion was detected on Cu–O3 bond length (2.473 Å). The Cu(II) centers lie in the center of the square (N, O, Cl, N), the O3 atom is positioned perpendicular to such a square plane giving a slightly distorted-square pyramid (cf. the figure).

References

Bruker. APEX2, SAINT and SADABS. Brucker AXS Inc., Madison, WI, USA (2012).Search in Google Scholar

Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

Glotova, T.; Dvorko, M.; Ushakov, I.; Chipanina, N.; Kazheva, O.; Chekhlov, A.; Dyachenko, O.; Gusarova, N.; Trofimov, B.: Chemo-, regio- and stereospecific addition of amino acids to acylacetylenes: a facile synthesis of new N-acylvinyl derivatives of amino acids. Tetrahedron 65 (2009) 9814–9818.10.1016/j.tet.2009.09.069Search in Google Scholar

Govindhan, R.; Karthikeyan, B.: Nano Cu interaction with single amino acid tyrosine derived self-assemblies; study through XRD, AFM, confocal Raman microscopy, SERS and DFT methods. J. Phys. Chem. Solids 111 (2017) 123–134.10.1016/j.jpcs.2017.07.025Search in Google Scholar

Li, A.; Liu, Y.; Yuan, L.; Ma, Z.; Zhao, C.; Xie, C.; Bao, W.; Xu, J.: Association of structural modifications with bioactivity in three new copper(II) complexes of Schiff base ligands derived from 5-chlorosalicylaldehyde and amino acids. J. Inorg. Biochem. 146 (2015) 52–60.10.1016/j.jinorgbio.2015.02.013Search in Google Scholar PubMed

Warad, I.; Abdoh, M.; Al Ali, A.; Shivalingegowda, N.; Kumara, K.; Zarrouk, A.; Lokanath, N.: Synthesis, spectra and X-ray crystallography of dipyridin-2-ylmethanone oxime and its CuX2(oxime)2 complexes: Thermal, Hirshfeld surface and DFT analysis. J. Mol. Struct. 1154 (2018) 619–625.10.1016/j.molstruc.2017.10.087Search in Google Scholar

Hoskins, B.; Robson, R.: Infinite polymeric frameworks consisting of three dimensionally linked rod-like segments. J. Am. Chem. Soc. 111 (1989) 5962–5964.10.1021/ja00197a079Search in Google Scholar

Ferrando-Soria, J.; Cangussu, D.; Eslava, M.; Journaux, Y.; Lescouëzec, R.; Julve, M.; Lloret, F.; Pasán, J.; Ruiz-Pérez, C.; Lhotel, E.; Paulsen, C.; Pardo, E.: Rational enantioselective design of chiral hetero-bimetallic single-chain magnets: synthesis, crystal structures and magnetic properties of oxamato-bridged MIICuII chains (M = Mn, Co). Chem. Eur. J. 17 (2011) 12482–12494.10.1002/chem.201101459Search in Google Scholar PubMed

Hong, J.; Huo, L.; Wang, Y.; Long, R.; Zheng, C.: Syntheses, crystal structures and properties of two coordination polymers derived from flexible dicarboxylate and N-donor ligands. Inorg. Chim. Acta 455 (2017) 81–87.10.1016/j.ica.2016.10.016Search in Google Scholar

Bloch, E.; Queen, W.; Hudson, M.; Mason, J.; Xiao, D.; Murray, L.; Flacau, R.; Brown, C.; Long, J.: Hydrogen storage and selective, reversible O2 adsorption in a metaleorganic framework with open chromium(II) sites. Angew. Chem. Int. Ed. 55 (2016) 8605–8609.10.1002/anie.201602950Search in Google Scholar PubMed

Received: 2017-12-6
Accepted: 2018-2-26
Published Online: 2018-3-10
Published in Print: 2018-5-24

©2018 Mouslim Messali et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Articles in the same Issue

  1. Cover and Frontmatter
  2. Bis(tetraethylammonium) carbonate – boric acid – water (1/2/5), C17H56B2N2O14
  3. Crystal structure of 4-methoxy-6-phenyl-2H-pyran-2-one, C12H10O3
  4. Crystal structure of tris{(3-((E)-(((E)-2-oxidobenzylidene)hydrazono)methyl)-2-oxo-2H-chromen-4-olato-κ3O,N:N′)}dicobalt(III)tris(dimethylformamide), C60H50Co2N9O15
  5. Crystal structure of poly[bis(1-methyl-[4,4′-bipyridin]-1-ium-κN)-tetrakis(μ3-sulfato-κ3O:O′:O′′)trizinc(II)], C22H22Zn3N4O16S4
  6. Crystal structure of (5Z,10Z)-3,13-dichloro-17,18-dioxo-5,11-diphenyl-8,9,17,18-tetrahydro-7H-dibenzo[e,n][1,4,8,12]tetraazacyclopentadecine-16,19-diido-κ4N,N′,N′′,N′′′)copper(II), C31H22N4O2Cl2Cu
  7. Crystal structure of bis{5-methoxy-2-(((2-oxo-2H-chromen-6-yl)imino)methyl)phenolato-κ2N,O}zinc(II), C34H24N2O8Zn
  8. Crystal structure of 2,2′-((((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))diphenolato-κ2N4O)nickel(II), C28H22N2O4Ni
  9. Crystal structure of 1,1′-((1E,1′E)-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(naphthalen-2-olato)cobalt(II), C36H26N2O4Co
  10. Crystal structure of camptothecin, C20H16N2O4
  11. Crystal structure of (2-(chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato–κ2O,O′)(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, Ni(C16H36N4)(C12H12O4Cl)ClO4⋅H2O
  12. Crystal structure of 3-(2-chloro-6-methoxyquinolin-3-yl)-5-phenylisoxazole (C19H13ClN2O2)
  13. Crystal structure of tetrakis(μ2-acetato-κ2O:O′)-bis{[(E)-2,6-diisopropyl-N-(pyridin-3-ylmethylene)aniline]copper (II)}, C44H56Cu2N4O8
  14. Crystal structure of diethyl 2-(2-chlorophenyl)-1,3-dioxane-5,5-dicarboxylate, C16H19Cl1O6
  15. Crystal structure of (μ2-2,2′-bipyridine-3,3′-dicarboxylato)-bis(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane)-di-nickel(II) perchlorate N,N′-dimethylformamide solvate, C50H92Cl2N12Ni2O14
  16. Crystal structure of catena-poly[triaqua(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′)-(1,2-bis(4-pyridyl)ethane-κN)nickel(II)] 2-aminonicotinate nitrate – 1,2-bis(4-pyridyl)ethane – water (2/1/8), C36H44N8NiO12
  17. Hydrothermal synthesis and crystal structure of poly[bis(μ2-3-(3,5-dicarboxyphenoxy)phthalato-κ3O,O′:O′′)-(μ2-1,2-di(pyridin-4-yl)ethane-κ2N:N′)copper(II)], C22H14CuNO9
  18. Crystal structure of catena-poly[aqua-(methanol-κO)-bis(μ2-4-(pyridin-4-yl)benzoato-κ2N:O)-bis(triphenylphospine-κP)disilver(I)], C61H52Ag2N2O6P2
  19. The crystal structure of 6-(4-bromobenzyl)-1,3,5-trimethyl-7-phenyl-1,5-dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-dione, C22H20BrN3O2
  20. Synthesis and crystal structure of catena-poly[bis(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetato-κO2O′,O′′)-(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)zinc(II)], C44H32N4ZnCl4O4
  21. Crystal structure of diaqua-bis[N-phenyl-2-(quinolin-8-yloxy)acetamide-κ3-N,O,O′]-nitrato(κ2O,O′)-cerium(III) dinitrate - acetone (1/2), C40H44N7O17Ce
  22. Crystal structure of the 2D coordination polymer poly[aqua(μ2-2,2′-(1,2-phenylene)diacetato-κ3O,O′:O′)-(μ2-4,4′-bis((1H-1,2,4-triazol-1-yl)methyl)-1,1′-biphenyl-κ2N:N′)cobalt(II)], C28H26CoN6O5
  23. Crystal structure of (dimethylformamide-κO)(perchlorato-κ2O,O′){μ2-6,6′-((1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(4-bromo-2-methoxyphenolate)-κ8N,N′,O:O,O′:O′,O′′,O′′′}sodium(I)nickel(II), C25H23Br2ClN3NaNiO9
  24. The crystal structure of catena-poly[bis((4-aminophenyl)sulfonyl)(pyrimidin-2-yl)amido-κ2N,N′)-bis(μ2-4,4′-bipyridine-N,N′2N:N′)zinc(II) – methanol (1/2), C32H34N10O6S2Zn
  25. Synthesis and crystal structure poly[aqua(μ3-2-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)acetate-κ4O,O′:O′′:O′′′) sodium] monohydrate, C18H18NNaO11S
  26. Crystal structure of methyl 4′-amino-3′,5′-diisopropyl-[1,1′-biphenyl]-4-carboxylate, C20H25NO2
  27. Crystal structure of (η6-1-isopropyl-4-methyl benzene)-(N-(2,5-dichlorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) perchlorate, C22H22Cl4N2O4Ru
  28. Crystal structure of 2-(2-(1-Chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1H-1,2,4-triazole-3(2H)-thione, C14H15Cl2N3OS
  29. Crystal structure of methyl 4′-amino-3′,5′-dimethyl-[1,1′-biphenyl]-4-carboxylate, C16H17NO2
  30. The crystal structure of 1-(5-ferrocenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pentan-1-on, C19H19F3FeN2O
  31. The crystal structure of (3S,12R,20R,24S)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25-triol acetone solvate, C34H56O6
  32. Crystal structure of methyl 10-(pyridin-4-yl)-anthracene-9-carboxylate, C21H15NO2
  33. Crystal structure of catena-poly[diaqua-bis(di(N2,N6-dihydroxypyridine-2,6-dicarboxamide))potassium(I)]tetrahydrate, C14H25N6O14K
  34. Crystal structure of poly{[μ2-(E)-1,4-bis(1H-benzo[d]imidazol-1-yl)but-2-ene-κ2N:N′][μ3–cyclohexane-1,4-dicarboxylato-κ4O,O′:O′′:O′′′]cadmium(II)}, C26H26CdN4O4
  35. Crystal structure of poly[aqua(μ3-[2,2′-bipyridine]-3,3′-dicarboxylato-κ4N,N′:O:O′)zinc(II)] – dimethylformamide (1/1), C15H15N3O6Zn
  36. The crystal structure of poly[tetraaqua-tris(μ2-2,6-di(1H-imidazol-1-yl)naphthalene-κ2N:N′)-bis(thiophene-2,5-dicarboxylato-κ1O)]dicobalt(II), C30H24CoN6O6S
  37. Crystal structure of (S)-1-(5-(anthracen-9-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O
  38. Crystal structure of 5-methyl-3,3-diphenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C25H25NO2S
  39. Synthesis and crystal structure of μ-[1,1′-di(mesitylphosphanido)ferrocene]bis[η5-cyclopentadienylnickel(II)] tetrahydrofurane solvate, C42H48FeNi2OP2
  40. Synthesis and crystal structure of (E)-1-(4-(((E)-5-chloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15ClN2O2
  41. Crystal structure of bis(1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O)nickel(II), C24H22N8O4S2Ni
  42. Crystal Structure of bis(1-(phenylsulfonyl)-2-(1-(pyrazin-2-yl)ethylidene)hydrazin-1-ido-κ3N,N′,O)copper(II), C24H22N8O4S2Cu
  43. Synthesis and crystal structure of poly[aqua{μ3-(1S,2S)-1-((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)pyrrolidin-1-ium-2-carboxylato-κ4O,O′:O′′:O′′′}sodium(I)] monohydrate, C21H22NNaO11S
  44. Halogen bonds in the crystal structure of 1,4-diiodotetrafluorobenzene–1,2-bis(4-pyridyl)propane (1/1), C19H14F4I2N2
  45. Crystal structure of bis(μ-N-i-propyl-N-n-propyldithiocarbamato-κ2S:S′) bis(N-i-propyl-N-n-propyldithiocarbamato-κ2S,S′)dizinc(II), C28H56N4S8Zn2
  46. Crystal structure of bis(μ-N-i-propyl-N-n-propyldithiocarbamato-κ3S,S′:S)bis(N-i-propyl-N-n-propyldithiocarbamato-κ2S,S′)dicadmium(II), C28H56Cd2N4S8
  47. Crystal structure of bis(μ2-di-n-butyldithiocarbamato-κ3S,S′:S3S:S:S′)-hexacarbonyl-di-rhenium(I), C24H36N2O6Re2
  48. Crystal structure of 7-(4-methylphenyl)imidazo[1,2-a][1,3,5]triazin-4-amine, C12H11N5
  49. Crystal structure of the co-crystal O-isopropyl phenylcarbamothioate – 4,4′-bipyridine (2/1), C15H17N2OS
  50. Crystal structure of the coordination polymer catena-poly[chlorido-{μ2-2-(((3,5-dimethyl-1H-pyrazol-1-yl)methyl)amino)-3-hydroxybutanoato-κ4N,N,O:O′}copper(II)], C11H16ClCuN2O3
  51. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-di(ethanol)-bis{μ2-5-(N,N′-diethylamine)-5′-methoxyl-2,2′-[ethylenediyldioxybis(nitrilomethylidyne)]diphenolato-κ6O:O,N,N,O′:O′}trinickel(II) – ethanol – acetonitrile (1/2/2), C58H86Ni3N8O18
  52. Crystal structure of the bis((E)-O-ethyl-N-phenylthiocarbamate) – 4,4′-bipyridine co-crystal (2/1), C28H30N4O2S2
  53. Crystal structure of the (E)-O-methyl-N-phenyl-thiocarbamate – 4,4′-bipyridine (1/1), C18H17N3OS
  54. Crystal structure of bis(μ2-diethyldithiocarbamato-κ3S,S′:S′)-bis(tricyclohexylphosphane-κP)dicopper(I), C46H86Cu2N2P2S4
  55. Crystal structure of N-(3-chlorophenyl)ethoxycarbothioamide, C9H10ClNOS
  56. Crystal structure of bis(μ2-pyrrolidine-1-carbodithioato-κ3S,S′:S;κ3S:S:S′)-bis(tricyclohexylphosphane-P)-di-copper(I), C46H82Cu2N2P2S4
  57. Crystal structure of N-(2-chlorophenyl)methoxycarbothioamide, C8H8ClNOS
  58. Crystal structure of chlorido-methanol-(N-(2-(oxy)-3-methoxybenzylidene)pyridine-4-carbohydrazonato-κ3O,N,O′)-(4-methylphenyl)methyl-tin(IV), C23H24ClN3O4Sn
  59. Crystal structure of N-(3-chlorophenyl)(propan-2-yloxy)carbothioamide, C10H12ClNOS
  60. Crystal structure of 1-[(Z)-[4-(4-methoxyphenyl)butan-2-ylidene]amino]-3-phenylurea, C18H21N3O2
  61. A triclinic polymorph of bis(μ-N,N-bis(2-hydroxyethyl)dithiocarbamato-κ3S,S′:S′) bis(N,N-bis(2-hydroxyethyl)dithiocarbamato-κ2S:S′)zinc(II), C20H40N4O8S8Zn2
Downloaded on 21.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2017-0383/html
Scroll to top button