Startseite Crystal structure of di-μ-iodido-bis(6-(p-tolyl)-2,2′-bipyridine-κ2N,N′)dicopper(I) — 2-(diphenylphosphoryl)benzoic acid (1/2), C36H29CuIN2O3P
Artikel Open Access

Crystal structure of di-μ-iodido-bis(6-(p-tolyl)-2,2′-bipyridine-κ2N,N′)dicopper(I) — 2-(diphenylphosphoryl)benzoic acid (1/2), C36H29CuIN2O3P

  • Shengyun Yang und Gang Yao EMAIL logo
Veröffentlicht/Copyright: 18. August 2017

Abstract

C36H29CuIN2O3P, triclinic, P1̅ (no. 2), a = 9.4713(3) Å, b = 11.8586(4) Å, c = 14.7597(5) Å, α = 93.5250(10)°, β = 90.61(10)°, γ = 108.99(10)°, V = 1563.71(9) Å3, Z = 2, Rgt(F) = 0.0279, wRref(F2) = 0.0688, T = 293 K.

CCDC no.:: 1564625

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:Yellow single crystals
Size:0.25 × 0.2 × 0.1 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.78 mm−1
Diffractometer, scan mode:CCD area detector, ϕ and ω scans
θmax:28.2°
N(hkl)measured, N(hkl)unique, Rint:11899, 6810, 0.018
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5193
N(param)refined:398
Programs:Bruker SMART, SAINT [4], SHELX [5]
Table 2

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

AtomxyzUiso*/Ueq
I10.202358(17)0.149018(15)0.455673(11)0.04863(7)
Cu1−0.05539(3)−0.01061(3)0.420358(18)0.04417(9)
P10.62328(7)0.27130(6)0.13007(4)0.03666(14)
O10.47814(19)0.17238(15)0.13022(11)0.0460(4)
N2−0.2275(2)0.01138(16)0.33889(12)0.0347(4)
O20.6287(2)0.11778(16)−0.03034(11)0.0560(5)
O30.7194(2)−0.03213(16)−0.01650(12)0.0545(5)
H30.6585−0.0644−0.05790.082*
N1−0.0349(2)−0.10711(18)0.30224(13)0.0412(5)
C180.7908(3)0.2271(2)0.14072(14)0.0354(5)
C250.6319(3)0.3769(2)0.22558(14)0.0359(5)
C310.6443(3)0.3567(2)0.03063(15)0.0403(5)
C11−0.2880(2)0.1557(2)0.44203(15)0.0387(5)
C10.0744(3)−0.1524(2)0.28324(18)0.0517(7)
H1B0.1486−0.14370.32740.062*
C6−0.2591(3)−0.0655(2)0.26424(14)0.0378(5)
C16−0.1443(3)0.2361(2)0.45245(16)0.0440(6)
H16A−0.07080.22760.41400.053*
C350.5254(4)0.4111(3)−0.09626(19)0.0656(9)
H35A0.43960.4027−0.13090.079*
C5−0.1417(3)−0.1183(2)0.23842(15)0.0386(5)
C7−0.3934(3)−0.0929(2)0.21540(16)0.0491(6)
H7A−0.4120−0.14450.16340.059*
C13−0.3559(3)0.2627(3)0.56904(19)0.0597(8)
H13A−0.42830.27070.60870.072*
C12−0.3940(3)0.1698(3)0.50281(18)0.0505(6)
H12A−0.49100.11630.49860.061*
C290.7384(3)0.5672(2)0.30983(19)0.0551(7)
H29A0.80920.64320.31570.066*
C200.9505(3)0.1135(2)0.09429(16)0.0453(6)
H20A0.96890.05580.05500.054*
C190.8201(3)0.1405(2)0.08222(14)0.0374(5)
C15−0.1085(3)0.3287(2)0.51909(18)0.0528(7)
H15A−0.01130.38180.52420.063*
C260.5284(3)0.3423(2)0.29182(17)0.0505(6)
H26A0.45690.26660.28640.061*
C360.5160(3)0.3468(2)−0.01990(17)0.0519(7)
H36A0.42370.2971−0.00260.062*
C221.0239(3)0.2523(2)0.22270(16)0.0457(6)
H22A1.09100.28920.27050.055*
C14−0.2132(3)0.3443(3)0.57815(18)0.0556(7)
C280.6355(4)0.5309(3)0.37571(19)0.0671(8)
H28A0.63720.58170.42660.081*
C9−0.4674(3)0.0344(2)0.31997(17)0.0475(6)
H9A−0.53830.06790.34060.057*
C240.7113(3)0.0750(2)0.00626(15)0.0414(6)
C10−0.3291(3)0.0631(2)0.36593(15)0.0375(5)
C300.7373(3)0.4917(2)0.23515(16)0.0450(6)
H30A0.80710.51710.19060.054*
C230.8939(3)0.2806(2)0.21178(15)0.0411(6)
H23A0.87500.33640.25270.049*
C4−0.1386(3)−0.1747(2)0.15345(16)0.0507(6)
H4A−0.2117−0.18060.10920.061*
C20.0817(3)−0.2113(3)0.2012(2)0.0602(8)
H2A0.1580−0.24320.19040.072*
C211.0538(3)0.1700(2)0.16316(17)0.0475(6)
H21A1.14220.15260.16910.057*
C320.7788(3)0.4311(3)0.00403(18)0.0623(8)
H32A0.86580.43740.03670.075*
C8−0.4976(3)−0.0436(3)0.24429(17)0.0520(7)
H8A−0.5888−0.06270.21280.062*
C3−0.0265(3)−0.2218(3)0.13566(19)0.0601(8)
H3A−0.0238−0.26060.07930.072*
C340.6582(4)0.4857(3)−0.12060(19)0.0698(9)
H34A0.66300.5297−0.17120.084*
C17−0.1736(4)0.4480(3)0.6487(2)0.0895(11)
H17A−0.22980.42420.70210.134*
H17B−0.19700.51360.62500.134*
H17C−0.06870.47230.66410.134*
C330.7861(4)0.4972(3)−0.0712(2)0.0811(11)
H33A0.87750.5490−0.08810.097*
C270.5299(4)0.4192(3)0.3663(2)0.0734(9)
H27A0.45880.39520.41040.088*

Source of material

6-(4-methanylphenyl)-2,2′-bipyridine was prepared by a literature method [3]. CuI and 2-(diphenylphosphinyl)-benzoic were commercial available. Equivalent amount (1 mmol) of CuI, 6-(4-methanylphenyl)-2,2′-bipyridine and 2-(diphenylphosphinyl)benzoic acid were added to 30 mL dichloromethane under a nitrogen atmosphere. The mixture was reacted for 2 h at room temperature. Then the solvent was removed. Yellow crystals were obtained from the solution of dichloromethane by vapor diffusion with diethyl ether.

Experimenal details

H atoms on C atoms were positioned geometrically refined using a riding model with C—H = 0.93–0.96 Å, and Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C). The hydrogen atom in the carboxyl group was fixed to OH distances of 0.82(1) Å [Uiso(H) = 1.2Ueq(O)].

Comment

Copper(I) complexes with bipyridine ligands have attracted much attention for their low-lying charge-transfer (CT) excited states, and potential applications in electrochemical devices and in solar energy conversion [1]. In addition, 2-(diphenylphosphinyl)benzoate is also a useful ligand in transitional metal complexes, and has been used for the construction of coordination polymers [2]. We intended to synthesize a polynuclear copper(I) complex using two different ligands. But unexpectely, the title complex was obtained.

The asymmetric unit of the title crystal structure contains the coordinated 2-(diphenylphosphoryl)benzoic acid and one half of a (C17H14N2)2Cu(μ-I)2 complex. Each copper(I) adopts a distorted tetrahedral coordination (neglection of the Cu-Cu interaction), with the N1—Cu1—N2 and I1—Cu1—I1A angles of 79.80(7) and 121.94(1)°, respectively. The Cu—N and Cu—I distances are within the normal ranges [3]. In addition, a Cu-Cu interaction was found in the title compound, with the Cu1—Cu1A distance of 2.5287(5) Å. Owing to the chelate effect, the two pyridine ring moieties are almost coplanar [dihedral angle of 16.5(1)°], while the pendant aromatic ring is twist with the adjacent pyridine fragment [dihedral angle of 37.7(1)°].

References

Williams, R. M.; Cola, L. D.; Hartl, F.; Lagref, J. J.; Planeix, J. M.; Cian, A. D. M.; Hosseini, W.: Photophysical, electrochemical and electrochromic properties of copper-bis (4,4′-dimethyl-6,6′-diphenyl-2,2′-bipyridine) complexes. Coord. Chem. Rev. 230 (2002) 253–261.10.1016/S0010-8545(02)00046-2Suche in Google Scholar

Zhou, M.; Song, L.; Niu, F.; Shu, K.; Chai, W.: A square-pyramidal copper(II) complex with strong intramolecular hydrogen bonds: diaqua(N, N′-dimethylformamide-O) bis[2-(diphenylphosphoryl) benzoato-O] copper(II). Acta Crystallogr C69 (2013) 463–466.10.1107/S0108270113008317Suche in Google Scholar PubMed

Cao, Q.-Y.; Gan, X.; Fu, W.-F.: Synthesis, characterization, spectroscopic and electrochemical properties of new mono- and binuclear copper(I) complexes with substituted 2,2′-bipyridine. Chin. J. Chem. 22 (2004) 1283–1287.10.1002/cjoc.20040221114Suche in Google Scholar

Bruker. SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA, 2007.Suche in Google Scholar

Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Suche in Google Scholar PubMed

Received: 2017-3-13
Accepted: 2017-7-25
Published Online: 2017-8-18
Published in Print: 2017-9-26

©2017 Shengyun Yang et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of 2-(2-ethoxyphenyl)-7-propyl-5-methylimidazo[5,1-f][1,2,4]triazin-4(3H)-one, C17H20N4O2
  3. Crystal structure of catena-poly[aqua-(μ3-1,3,5-benzenetricarboxylato-κ3O:O′:O′′)-[μ3hydroxy-(1,3-di-(μ2-1,2,4-triazole-4-yl)benzoato-κ2N:N′)copper(II)], C19H16Cu2N6O9
  4. Crystal structure of poly[aqua-(μ3-3,5-di(4H-1,2,4-triazolyl-4-κ3N,N′:N′′)benzenecarboxylato)silver(I)], C11H9AgN6O3
  5. Crystal structure of tetrapropylammonium hydrogen carbonate, C13H29NO3
  6. Crystal structure of poly[μ2-acetato-κ3-O,O′:O′)diaqua(μ3-isophthalato-κ4O,O′:O′′:O′′′)yttrium(III)] monohydrate, C20H24O17Y2
  7. Crystal structure of catena-poly[dichlorido-(μ2-4-(1H-pyrazol-3-yl)-pyridine-κ2N,N′)]cadmium(II), C48H42Cd3Cl16N18
  8. Crystal structure of bis(tetraethylammonium) [1,1′-biphenyl]-2,2′-dicarboxylate trihydrate, C30H54N2O7
  9. Crystal structure of poly[(thiophene-3,4-dicarboxylato-κ1O)bis[1,2-bis(4-pyridyl)ethane-κ2N:N′]silver(I)] octahydrate, C30H42Ag2N4O12S
  10. The crystal structure of amine-(4-(1H-1,2,4-triazol-1-yl)benzoato-κN)silver(I) dihydrate, C9H13AgN4O4
  11. Crystal structure of poly[tetrakis(μ2-cyanido-κ2N:O)-cyanido-tris(pyridine)dicobalt(II/III)], C20H15Co2N8
  12. Crystal structure of bis(pyridine)-bis(2-formyl-4,6-dichlorophenolato)cobalt(II), C24H16Cl4CoN2O4
  13. Crystal structure of (E)-1-(4-(((E)-5-bromo-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15BrN2O2
  14. Crystal structure of catena-poly[(μ2-3-(1H-pyrazol-4-yl)-5-(pyridin-4-yl)-1,2,4-triazole-κ N:N′)-bis(benzoato-κO)zinc(II)], C24H18N6O4Zn
  15. Hydrothermal synthesis and crystal structure of a poly[aqua-(μ4-4-(carboxylatomethyl)benzoato-κ4O:O′:O′′:O′′′)-(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′) dimanganese(II)], [Mn2(C9H6O4)2(C12H11N5)(H2O)]
  16. Crystal structure of diaqua-catena-poly[diaqua-bis(μ2-5-(4-(1H-1,2,4-triazol-1-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)] dihydrate, C20H24CoN14O4
  17. Crystal structure of bis(μ3-2,2′-azanediylbis(ethan-1-olato)-κ5O:O,N,O′:O′)-tetrachlorido-bis(μ2-2-((2-hydroxyethyl)amino)ethan-1-olato-κ3N,O:O)dicobalt(II)dicobalt(III), C16H38Cl4Co4N4O8
  18. Crystal structure of poly[μ4-(4-(carboxylatomethyl)benzoato-κ4O:O′:O′′:O′′′)-(2-(4-(1H-imidazol-1-yl)phenyl)-1H-benzo[d]imidazole-κN)manganese(II)] [Mn(C9H6O4)(C16H12N4)]
  19. Crystal structure of 4-chloro-6-phenylpyrimidine, C10H7ClN2
  20. The crystal structure of [6-methoxy-2-(2,2,2-trifluoroacetyl)-3,4-dihydronaphthalen-1(2H)-one]difluoroborane, C13H10BF5O3
  21. Crystal structure of 3,3′-(butane-1,4-diylbis(azanylylidene))bis(1-phenylbut-1-en-1-olato)-κ4N,N′,O,O′]copper(II), C24H26N2O2Cu
  22. Crystal structure of tetraaqua-bis((E)-N′-(2-bromobenzylidene)isonicotinohydrazide-κN)zinc(II) dinitrate, C26H28N8O12Br2Zn
  23. Crystal structure of 2-amino-4-(4-bromophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H13BrN2O2
  24. A single crystal study on tert-butyl-4-((4-(4-bromo-2-fluorophenylamino)-6-methoxyquinazolin-7-yloxy)methyl)piperidine-1-carboxylate, C26H30BrFN4O4
  25. 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-κ3O,O′,N)zinc(II), C36H26N2O4Zn
  26. Crystal structure of diaqua-bis(5′-(pyridin-1-ium-4-yl)-1H-[3,3′-bi(1,2,4-triazol)]-2′-ide-κ2N,N′)cobalt(II) — bis(5-(pyridin-4-yl-κN)-1H,1′H-3,3′-bi(1,2,4-triazole))octamolybdate – water (2/1/8), C27H33CoMo4N21O19
  27. Crystal structure of 3-cyclohexyl-2-(cyclohexylimino)-2,3-dihydro-6,8-diiodo-4H-1,3-benzoxazin-4-one, C20H24I2N2O2
  28. Crystal structure of dinitrato-κO-bis(tris((1H-benzo[d]imidazol-2-yl)methyl)amine-κ4N,N′,N′′,N′′′)-(μ2-cyclohexane-1,4-dicarboxylato-κ4O,O′:O′′,O′′′)dimanganese(II) – methanol – water (1/6/2), C62H80Mn2N16O18
  29. Crystal structure of bis(2-hydroxyethyl(phenyl)carbamodithioate)nickel(II), C18H20N2NiO2S4
  30. Crystal structure of methyl 1-(4-fluorobenzyl)-4-methoxy-5-oxopyrrolidine-3-carboxylate, C14H16FNO4
  31. Crystal structure of di-μ-iodido-bis(6-(p-tolyl)-2,2′-bipyridine-κ2N,N′)dicopper(I) — 2-(diphenylphosphoryl)benzoic acid (1/2), C36H29CuIN2O3P
  32. Crystal structure of 2-amino-4-(3-bromo-4-fluoro-phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C18H16BrFN2O2
  33. Crystal structure of bis(μ2-2-chlorobenzoato-κ3O,O′:O′)-(2-chlorobenzoato-κO)-(2-chlorobenzoato-κO,O′)-bis(1,10-phenanthroline-κ2N,N′)-dicadmium(II) monohydrate, C52H36Cd2Cl4N4O10
  34. Crystal structure of 2-(8a-methyl-5-oxo-hexahydroimidazo [1,2-a]pyridin-1(5H)-yl)-2-oxoethyl acetate, C12H18N2O4
  35. Crystal structure of (E)-N,N-diethyl-2-(5-nitrothiazol-2-yl)-1-phenylethen-1-amine, C15H17N3O2S
  36. Crystal structure of diazido-dimethanolato-bis(μ2-2-(((3-oxidopropyl)imino)methyl)phenolato-κ4O:O,O′,N)dimanganese(III), C22H28Mn2N8O6
  37. The crystal structure of bis(2-(2,2,2-trifluoroacetyl)-3,4-dihydronaphthalen-1-olato-κ2O,O′)copper(II), C24H16CuF6O4
  38. Crystal structure of hexaaquanickel(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C28H40N6NiO12S2
  39. Crystal structure of catena-poly[aqua-(μ2-hexamethylenetetramine-κ2N:N′)-bis(2,6-difluorobenzoato-κ2O:O′)cadmium(II)]monohydrate, C20H22CdF4N4O6
  40. Crystal structure of 3-benzyl-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C15H12N2OS
  41. Crystal structure of bis(μ2-ferrocenecarboxylato-κ2O:O′)-bis(1,10-phenanthroline-κ2N,N′)-(μ2-methanolato2O,O)dicopper(II) tetrafluoroborate – acetonitrile (1/1), C49H40BCu2F4Fe2N5O5
  42. The crystal structure of tetrakis(1,3,5-triaza-7-phosphatricyclo[3.3.1.13,7]decane-κP)silver(I) chloride dihydrate, C24H60AgClN12O6P4
  43. Crystal structure of 5-ethyl-2-(p-tolyl)-1,3-dioxane-5-carboxylic acid, C14H18O4
  44. Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16ClIN2
  45. Crystal structure of catena-poly[(μ2-hexamethylenetetramine-κ2N:N′)-tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)dicopper(II)], C34H24Cu2F8N4O8
  46. Crystal structure of ethyl 3-hydroxy-5-methyl-2-(4-(m-tolyl)-1H-1,2,3-triazol-1-yl)-[1,1′-biphenyl]-4- carboxylate, C25H24N3O3
  47. The crystal structure of carbonyl(2-oxopyridin-1(2H)-olato-κ2O,O′)-(diphenylcyclohexylphosphine-κP)rhodium(I), C24H25NO3PRh
  48. Crystal structure of bis((pyrazin-2-ylmethyl)(pyrazine-2-carbonyl)amido-κ3N,N′,N′′)copper(II), C20H16CuN10O2
  49. Crystal structure of catena-poly[tetraaqua-(μ2-succinonitrile-κ2N:N′)cobalt(II)] dinitrate, C4H12CoN4O10
  50. The crystal structure of 1,1′-bisisoquinoline, C18H12N2
  51. Crystal structure of bis(hydroxydi(pyridin-2-yl)methanolato-κ3N,N′,O)cobalt(III) perchlorate dihydrate, C22H22ClCoN4O10
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