Home Crystal structure of catena-poly[(μ2-hexamethylenetetramine-κ2N:N′)-tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)dicopper(II)], C34H24Cu2F8N4O8
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Crystal structure of catena-poly[(μ2-hexamethylenetetramine-κ2N:N′)-tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)dicopper(II)], C34H24Cu2F8N4O8

  • Yuan Hou-Qun , Xiong You-Fa , Xiao Wei , Hu Chun-Yan and Bao Guang-Ming EMAIL logo
Published/Copyright: August 3, 2017
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 232 Issue 5

Abstract

C34H24Cu2F8N4O8, monoclinic, P21/n (no. 14), a =13.074(3) Å, b = 20.229(4) Å, c = 14.419(3) Å, β = 108.889(2)°, V = 3608.2(12) Å3, Z = 4, Rgt(F) = 0.0512, wRref(F2) = 0.1465, T = 296(2) K.

CCDC no.:: 1560964

A part of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Green needle
Size:0.15 × 0.10 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:12.8 cm−1
Diffractometer, scan mode:Bruker CCD, φ and ω
2θmax, completeness:56.8°, 98.7%
N(hkl)measured, N(hkl)unique, Rint:33606, 8923, 0.050
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5323
N(param)refined:498
Programs:Bruker programs [1], SHELX [2]
Table 2

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

AtomxyzUiso*/Ueq
Cu10.81154(4)0.28704(2)0.16716(3)0.03845(13)
Cu20.69321(4)0.20461(2)0.03194(3)0.03659(13)
O10.7756(2)0.35179(12)0.06081(19)0.0505(7)
C10.7297(3)0.33562(18)−0.0262(3)0.0407(8)
O20.6882(2)0.28056(12)−0.05585(18)0.0474(6)
C20.7254(3)0.38642(18)−0.1026(3)0.0474(9)
C30.6329(4)0.3987(2)−0.1803(3)0.0642(12)
F10.5449(2)0.36447(17)−0.1859(2)0.1021(11)
C40.6287(6)0.4457(3)−0.2517(4)0.0920(18)
H10.56490.4535−0.30260.110*
C50.7202(7)0.4799(3)−0.2451(5)0.107(2)
H20.71890.5109−0.29310.128*
C60.8137(6)0.4698(3)−0.1698(5)0.101(2)
H30.87580.4935−0.16620.121*
C70.8144(5)0.4249(3)−0.1008(4)0.0750(14)
F20.9072(3)0.4140(2)−0.0273(3)0.1231(14)
O30.9271(2)0.24890(14)0.1207(2)0.0538(7)
C80.9145(3)0.2049(2)0.0571(3)0.0495(10)
O40.8266(2)0.17840(14)0.0092(2)0.0558(7)
C91.0117(4)0.1800(3)0.0346(3)0.0601(12)
C101.0200(5)0.1152(3)0.0054(4)0.0797(15)
F30.9405(3)0.07354(18)−0.0003(4)0.1351(16)
C111.1086(6)0.0909(4)−0.0136(5)0.109(2)
H41.11110.0468−0.03110.131*
C121.1924(7)0.1317(5)−0.0068(6)0.135(3)
H51.25320.1152−0.01910.162*
C131.1896(6)0.1960(5)0.0177(7)0.131(3)
H61.24630.22440.01970.157*
C141.0989(5)0.2188(3)0.0401(6)0.100(2)
F41.0965(3)0.2831(2)0.0639(4)0.1477(19)
O50.6739(2)0.30572(14)0.1941(2)0.0536(7)
C150.5907(3)0.27400(18)0.1509(3)0.0436(9)
O60.5755(2)0.23955(13)0.07484(18)0.0469(6)
C160.5007(3)0.2741(2)0.1938(3)0.0504(10)
C170.4573(5)0.2165(3)0.2149(5)0.097(2)
C180.3792(6)0.2139(3)0.2576(6)0.116(3)
H70.35400.17320.27130.139*
C190.3383(5)0.2700(4)0.2801(5)0.103(2)
H80.28360.26860.30820.124*
C200.3765(6)0.3277(4)0.2621(5)0.110(2)
H90.34930.36690.27840.132*
C210.4554(5)0.3292(3)0.2198(5)0.0838(16)
O70.8285(2)0.21164(12)0.2549(2)0.0529(7)
C220.7839(3)0.15707(18)0.2271(3)0.0447(9)
O80.7267(2)0.14165(13)0.14296(19)0.0513(7)
C230.8007(4)0.1055(2)0.3051(3)0.0611(12)
C240.8319(4)0.0419(2)0.2940(4)0.0741(15)
F50.8464(3)0.02582(16)0.2104(3)0.1195(13)
C25Aa0.8639(9)−0.0091(5)0.3512(8)0.065(3)*
H11a0.8827−0.05000.33220.078*
C25Ba0.8407(9)−0.0018(6)0.3825(9)0.067(3)*
H12a0.8713−0.04360.38630.080*
C26Aa0.8654(11)0.0081(6)0.4482(10)0.083(3)*
H13a0.8845−0.02460.49600.100*
C26Ba0.8069(12)0.0181(7)0.4515(10)0.097(4)*
H14a0.8135−0.01200.50190.116*
C27Aa0.8407(12)0.0695(7)0.4753(10)0.097(4)*
H15a0.83840.07850.53790.116*
C27Ba0.7629(13)0.0770(7)0.4610(11)0.111(4)*
H16a0.73970.08710.51390.134*
C28Aa0.8189(10)0.1179(6)0.4009(8)0.074(3)*
C28Ba0.7551(10)0.1213(6)0.3851(8)0.076(3)*
F6Aa0.7947(7)0.1803(4)0.4238(6)0.114(2)*
F6Ba0.7119(7)0.1802(4)0.3880(6)0.106(2)*
N10.5802(2)0.14315(13)−0.07898(19)0.0342(6)
C290.6332(3)0.09934(18)−0.1318(3)0.0456(9)
H170.67320.1261−0.16410.055*
H180.68440.0710−0.08490.055*
N20.5554(3)0.05837(15)−0.2046(2)0.0520(9)
C300.4938(4)0.01888(19)−0.1549(3)0.0654(13)
H190.4415−0.0082−0.20290.079*
H200.5430−0.0105−0.10800.079*
N30.4376(3)0.06010(16)−0.1040(2)0.0540(9)
C310.5179(3)0.10028(19)−0.0323(3)0.0463(9)
H210.56750.07150.01510.056*
H220.48180.12790.00260.056*
C320.5036(3)0.18553(16)−0.1516(2)0.0329(7)
H230.54300.2131−0.18340.039*
H240.46730.2143−0.11850.039*
N40.4219(2)0.14643(13)−0.22678(19)0.0344(6)
C330.4799(3)0.10225(18)−0.2754(3)0.0472(9)
H250.42780.0758−0.32460.057*
H260.51950.1289−0.30820.057*
C340.3644(3)0.10398(19)−0.1754(3)0.0494(10)
H270.32680.1319−0.14220.059*
H280.31060.0777−0.22340.059*
F7Aa0.4713(7)0.3874(4)0.1734(6)0.103(2)*
F7Ba0.5128(5)0.3870(3)0.2247(5)0.0749(16)*
F8Aa0.4726(5)0.1590(3)0.1682(5)0.0746(16)*
F8Ba0.5227(6)0.1598(3)0.2194(5)0.0883(19)*

  1. aOccupancy: 0.50.

Source of materials

An aqueous solution (10 mL) of 2,6-difluorobenzoic acid (dfbaH) (315 mg, 2.0 mmol), NaHCO3 (160 mg, 2.0 mmol), and hexamethylenetetramine (70 mg, 0.5 mmol) was mixed with DMF/MeOH solution (10 mL) dissolving Cu(NO3)2⋅3H2O (300 mg, 2.2 mmol). The light blue solution was allowed to stand at room temperature to give green needle-like crystals within two weeks (yield 350 mg, 39% based on copper nitrate trihydrate).

Experimental details

Hydrogen atoms were placed in calculated positions and refined as riding on their parent atoms, with C—H = 0.93 Å (aromatic), C—H = 0.96 Å (methylene), and Uiso(H) = 1.2 Ueq(C).

Comment

Coordination polymers are of special interest because of their fascinating topological structures as well as their potential applications in many fields [3], [4], [5], [6], [7]. The self-assembly of organic molecules and metal ions construct a broad range of coordination polymers. The selection of organic ligands is a key point for rational design of targeted structures. A number of aromatic acids, especially aromatic multicarboxylates, have been used as bridging ligands. That is because the multicarboxylates not only have versatile coordination modes but also act as hydrogen bonding acceptors and donors [8]. Compared with the aromatic multicarboxylates, benzoic acid or its substituted derivatives possess a limited scope for the construction of coordination polymers [9]. However, polynuclear clusters with fascinating structures and properties which are constructed by benzoic acids have been reported [10, 11] . Meanwhile, the coordination polymers based on fluorine substituted organic molecules are found to be more stable to oxidation and show enhanced thermal stability [12].

On the other hand, the neutral N-containing heterocyclic molecules are ubquitously used as linker to construct coordination polymers. Lots of coordination polymers built from bipyridines and pyrazines are reported, while hexamethylenetetramine (hmt) was explored to a less extent [13]. However, hexamethylenetetramine has four coordinating N atoms which may link with different metal ions through various coordination modes that span from terminal monodentate to μ2-, μ3-, or μ4-bridging modes, which lead to one- (1D), two- (2D) and three-dimensional (3D) coordination polymers [14, 15] .

X-ray crystal structural analysis revealed that the asymmetric unit of the title complex is composed of two Cu2+ ions, four dfba− ligands and one hmt ligand. Each Cu2+ ion is coordinated in a square-pyramidal geometry with four oxygen atoms from four dfba− ligands and one nitrogen atom from a hmt ligand. The four oxygen atoms are located in the equatorial positions and the coordinated nitrogen atom is located at the axial position. The Cu2+ ions are deviated by 0.2179(14) Å for Cu1 and 0.2055(14) Å for Cu2 from the equatorial plane (defined by the four coordinated oxygen atoms) towards the axial N atoms, respectively. The four dfba− ligands using four carboxylate groups link two Cu2+ ions with distances of 2.6500(7) Å for Cu1⋯Cu2 to form the typical [Cu2(COO)4] paddlewheel building block. Hexamethylenetetramine ligands link the vertices of [Cu2(COO)4] paddlewheel units in a μ2-bridging mode. Therefore, a 1-D zigzag chain structure is formed in the structure of the title complex.

Acknowledgement

This work was supported by the National Nature Foundation of China [No. 21461011 and 31560712], the Natural Science Foundation of Jiangxi Province [No. 20112BBF60024, 20151BAB204014].

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Received: 2017-3-6
Accepted: 2017-7-13
Published Online: 2017-8-3
Published in Print: 2017-9-26

©2017 Yuan Hou-Qun et al., published by De Gruyter, Berlin/Boston

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

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  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
https://doi.org/10.1515/ncrs-2017-0064
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Articles in the same Issue

  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-methanolato-κ2O,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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