Home Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8
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Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8

  • Jaeun Kang , Minji Kim , Kang Min Ok and Junghwan Do EMAIL logo
Published/Copyright: April 7, 2017

Abstract

C28H38Cu2N6O8, monoclinic, P21/c (no. 14), a = 10.6191(1) Å, b = 14.6736(2) Å, c = 11.6519(2) Å, β = 111.056(1)°, V = 1694.38(4) Å3, Z = 2, Rgt(F) = 0.0298, wRref(F2) = 0.0871, T = 296 K.

CCDC no.:: 1541000

The crystal structure of the dinuclear title complex 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:Green Polyhedron
Size:0.28 × 0.25 × 0.19 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:13.1 cm−1
Diffractometer, scan mode:Bruker P4, ω-scans
2θmax, completeness:56.6°, >98%
N(hkl)measured, N(hkl)unique, Rint:15966, 4157, 0.044
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3380
N(param)refined:203
Programs:SHELX [1], DIAMOND [2]
Table 2

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

AtomxyzUiso*/Ueq
Cu1−0.065298(18)0.471150(12)0.887801(17)0.03058(8)
O10.09233(14)0.51463(10)0.85447(13)0.0481(3)
O2−0.20228(13)0.43497(11)0.95527(13)0.0504(3)
C10.19185(18)0.55255(12)0.93482(18)0.0383(4)
C20.3001(2)0.58318(14)0.8926(2)0.0508(5)
H20.28120.58020.80840.061*
C30.4217(2)0.61461(16)0.9604(2)0.0594(6)
C40.5192(3)0.6419(3)0.8986(3)0.0999(11)
H4A0.48690.61970.81550.150*
H4B0.60630.61620.94280.150*
H4C0.52610.70710.89820.150*
C50.4751(2)0.6254(2)1.0956(3)0.0768(8)
H5A0.40200.62351.12550.115*
H5B0.52090.68291.11680.115*
H5C0.53720.57691.13220.115*
O30.02746(13)0.35399(8)0.94601(11)0.0458(3)
O4−0.13974(13)0.59578(8)0.86499(12)0.0431(3)
C60.10646(16)0.34227(11)1.05433(16)0.0331(4)
C70.16402(18)0.25139(12)1.09685(17)0.0409(4)
H70.21650.24731.18000.049*
C80.1516(2)0.17537(13)1.03376(19)0.0539(5)
C90.2132(4)0.08883(16)1.0978(3)0.0928(10)
H9A0.23360.09531.18460.139*
H9B0.29470.07631.08290.139*
H9C0.15080.03951.06690.139*
C100.0742(4)0.16423(19)0.8992(2)0.1074(12)
H10A0.00260.20820.87310.161*
H10B0.03680.10390.88360.161*
H10C0.13350.17330.85450.161*
N1−0.17866(14)0.42116(10)0.69979(13)0.0361(3)
N2−0.37187(16)0.40935(11)0.51569(15)0.0472(4)
N3−0.36348(17)0.51460(12)0.66252(17)0.0582(5)
H3A−0.44260.53260.61640.070*
H3B−0.32300.54040.73240.070*
C11−0.30337(18)0.44661(12)0.62551(16)0.0376(4)
C12−0.12041(19)0.35552(13)0.65810(17)0.0463(5)
H12−0.03350.33750.70650.056*
C13−0.1820(2)0.31283(14)0.54706(19)0.0567(6)
H13−0.14020.26660.51930.068*
C14−0.3097(2)0.34315(14)0.47980(19)0.0563(6)
H14−0.35530.31550.40440.068*

Source of material

The mixture of CuCl2 (0.030 g, 0.3 mmol), 3,3–dimethylacrylic acid (0.031 g, 0.3 mmol), 2–aminopyrimidine (0.0860 g, 0.9 mmol) and ethanol (1.0 mL) was sealed under vacuum in a Pyrex tube and heated to 70 oC for 68 h, then cooled to room temperature at 20 oC/h. The pH before and after the reaction was 6̃. The solid products were recovered by vacuum filtration and washed with distilled water. Green polyhedral crystals were obtained together with unidentified green powder. The product is stable in air. The yield of the compound was about 30% based on copper.

Experimental details

H atoms were placed in calculated positions and refined as riding model. The Uiso value of the methyl group was set to 1.5Ueq(C) and the Uiso values of other H atoms were set to 1.2Ueq(C, N).

Discussion

Metal carboxylate complexes are one of the most important classes in coordination chemistry [3], [4], [5]. Especially, Cu(II) carboxylates with nitrogen donor ligands have been extensively studied due to their importance in biology and magnetism [6], [7], [8], [9]. In this study we report a new copper(II) complex containing 3,3–dimethylacrylate and 2–aminopyrimidine.

The crystal structure of the title compound comprises classical dimetallic Cu(II) paddle-wheel moiety. The dinuclear Cu(II) complex is positioned around a center of inversion. The two Cu(II) [d(Cu—Cu) = 2.6213(4) Å] are bridged by four 3,3–dimethylacrylato ligands. The four oxygen atoms around each Cu(II) form a distorted square planar geometry with the distance of 1.956(1)–1.976(1) Å. An additional nitrogen atom of the 2–aminopyrimidine [d(Cu—N) = 2.212(1) Å] completes the square pyramidal environment of Cu(II). The bond valence sum (BVS) calculation for Cu gives a value of + 2.04 [10]. The NH2 group forms a hydrogen bond with a neighbouring oxygen atom of a carboxylate group with the distance of 2.933(2) Å. In addition, each 2-aminopyrimidine forms weak NH⋯N (d = 3.043(2) Å) hydrogen bonds to the proton donating NH2–group and also to proton accepting N atom of the 2–minopyrimidine in an adjacent complex to complete one–dimensional chains. The interchain distance between the carbon atoms is > 3.61 Å, suggesting that van der Waals interactions predominate along the chain direction. The weakness of the interactions between the chains are reflected in the high thermal displacement parameters of the terminal carbon atoms of the 3,3–dimethylacrylate.

Acknowledgement

This paper was written as part of Konkuk University’s research support program for its faculty on sabbatical leave in 2016.

References

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

2 Brandenburg, K.: DIAMOND. Visual crystal structure information system. Version 4.2.2. Crystal Impact, Bonn, Germany, (2016).Search in Google Scholar

3 Eddaoudi, M.; Moler, D.; Li, H.; Chen, B.; Reineke, T. M.; O’Keeffe, M.; Yaghi, O. M.: Modular chemistry: Secondary building units as a basis for the design of highly porous and robust metal-organic carboxylate frameworks. Acc. Chem. Res. 34 (2001) 319–330.10.1021/ar000034bSearch in Google Scholar

4 Eddaoudi, M.; Li, H.; Yaghi, O. M.: Design, synthesis, structure, and gas (N2, Ar, CO2, CH4, and H2) sorption properties of porous metal-organic tetrahedral and heterocuboidal polyhedra. J. Am. Chem. Soc. 127 (2005) 7110–7118.10.1021/ja042802qSearch in Google Scholar

5 Wang, Z.; Kravtsov, V. C.; Zaworotko, M. J.: Ternary nets formed by self-assembly of triangles, squares, and tetrahedra. Angew. Chem. Int. Ed. 44 (2005) 2877–2880.10.1002/anie.200500156Search in Google Scholar

6 Kato, M.; Muto, Y.: Factors affecting the magnetic properties of dimeric copper(II) complexes. Coord. Chem. Rev. 92 (1988) 45–83.10.1016/0010-8545(88)85005-7Search in Google Scholar

7 Ferrer, S.; Lioret, F.; Beertmenu, I.; Alzuet, G.; Borras, J.; Garcia-Granda, S.; Liu-Gonzales, M.; Hassnoot, J. G.: Cyclic trinuclear and chain of cyclic trinuclear copper(II) complexes containing a pyramidal Cu3O(H) core. Crystal structures and magnetic properties of [Cu33-OH)(aaat)3(H2O)3](NO3)2⋅H2O [aaat = 3-acetylamino-5-amino-1,2,4-triazolate] and {[Cu33-OH)(aat)33-SO4)]⋅6H2O}n [aat = 3-acetylamino-1,2,4-triazolate]: New cases of spin-frustrated systems. Inorg. Chem. 41 (2002) 5821–5830.10.1021/ic020179+Search in Google Scholar PubMed

8 Christou, G.; Perlepes, S. P.; Libby, E.; Folting, K.; Huffman, J. C.; Webb, R. J.; Hendrickson, D. N.: Preparation and properties of the triply bridged, ferromagnetically coupled dinuclear copper(II) complexes [Cu2(OAc)3(bpy)2](ClO4) and [Cu2(OH)(H2O)(OAc)(bpy)2](ClO4)2. Inorg. Chem. 29 (1990) 3657–3666.10.1021/ic00344a008Search in Google Scholar

9 Holm, R. H.; Kennepohl, P.; Solomon, E. I.: Structural and functional aspects of metal sites in biology. Chem. Rev. 96 (1996) 2239–2314.10.1021/cr9500390Search in Google Scholar PubMed

10 Brese, N. E.; O’Keeffe, M.: Bond-valence parameters for solids. Acta Crystallogr. B47 (1991) 192–197.10.1107/S0108768190011041Search in Google Scholar

Received: 2016-10-27
Accepted: 2017-3-29
Published Online: 2017-4-7
Published in Print: 2017-5-24

©2017 Jaeun Kang 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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