Bis­{(E)-3-[2-(hy­droxy­imino)­propan­amido]-2,2-dimethyl­propan-1-aminium} bis[μ-(E)-N-(3-amino-2,2-dimethyl­prop­yl)-2-(hy­droxy­imino)­propanamido­(2−)]bis­{[(E)-N-(3-amino-2,2-dimethyl­prop­yl)-2-(hy­droxy­imino)­propanamide]­copper(II)} bis­((E)-{3-[2-(hy­droxy­imino)­propanamido]-2,2-dimethyl­prop­yl}carbamate) acetonitrile disolvate

Buvailo, A.I.; Pavlishchuk, A.V.; Penkova, L.V.; Kotova, N.V.; Haukka, M.

doi:10.1107/S160053681204620X

Volume 68
Part 12
Pages m1480-m1481
December 2012

Received 16 August 2012
Accepted 8 November 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.005 Å
R = 0.053
wR = 0.147
Data-to-parameter ratio = 18.0
Details

Bis{(E)-3-[2-(hydroxyimino)propanamido]-2,2-dimethylpropan-1-aminium} bis[-(E)-N-(3-amino-2,2-dimethylpropyl)-2-(hydroxyimino)propanamido(2-)]bis{[(E)-N-(3-amino-2,2-dimethylpropyl)-2-(hydroxyimino)propanamide]copper(II)} bis((E)-{3-[2-(hydroxyimino)propanamido]-2,2-dimethylpropyl}carbamate) acetonitrile disolvate

Andrii I. Buvailo,^a Anna V. Pavlishchuk,^a ^* Larysa V. Penkova,^a Natalia V. Kotova ^a and Matti Haukka ^b

^aDepartment of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska str. 62, Kiev 01601, Ukraine, and ^bUniversity of Joensuu, Department of Chemistry, PO Box 111, FI-80101 Joensuu, Finland
Correspondence e-mail: annpavlis@ukr.net

The reaction between copper(II) nitrate and (E)-N-(3-amino-2,2-dimethylpropyl)-2-(hydroxyimino)propanamide led to the formation of the dinuclear centrosymmetric copper(II) title complex, (C₈H₁₈N₃O₂)₂[Cu₂(C₈H₁₅N₃O₂)₂(C₈H₁₇N₃O₂)₂](C₉H₁₆N₃O₄)₂·2CH₃CN, in which an inversion center is located at the midpoint of the Cu₂ unit in the center of the neutral [Cu₂(C₈H₁₅N₃O₂)₂(C₈H₁₇N₃O₂)₂] complex fragment. The Cu²⁺ ions are connected by two N-O bridging groups [CuCu separation = 4.0608 (5) Å] while the Cu^II ions are five-coordinated in a square-pyramidal N₄O coordination environment. The complex molecule co-crystallizes with two molecules of acetonitrile, two molecules of the protonated ligand (E)-3-[2-(hydroxyimino)propanamido]-2,2-dimethylpropan-1-aminium and two negatively charged (E)-{3-[2-(hydroxyimino)propanamido]-2,2-dimethylpropyl}carbamate anions, which were probably formed as a result of condensation between (E)-N-(3-amino-2,2-dimethylpropyl)-2-(hydroxyimino)propanamide and hydrogencarbonate anions. In the crystal, the complex fragment [Cu₂(C₈H₁₅N₃O₂)₂(C₈H₁₇N₃O₂)₂] and the ion pair C₈H₁₈N₃O₂^+.C₉H₁₆N₃O₄^- are connected via an extended system of hydrogen bonds.

Related literature

For properties of polynuclear complexes, see: Krämer & Fritsky (2000); Fritsky et al. (2001, 2003); Thompson (2002); Wörl et al. (2005); Bauer-Siebenlist et al. (2005); Thallapally et al. (2010); Cui et al. (2012); Beauvais et al. (2000). For studies of dinuclear copper(II) catecholase activity, see: Demmin et al. (1991); Monzani et al. (1998). For use of 2-hydroxyiminopropanoic acid derivatives as versatile ligands, see: Fritsky et al. (1998, 2006); Kanderal et al. (2005); Moroz et al. (2008, 2010, 2012); For the [tau] parameter, see: Addison et al. (1984). For related structures, see: Duda et al. (1997); Dobosz et al. (1999); Mokhir et al. (2002); Onindo et al. (1995); Petrusenko et al. (1997); Sliva et al. (1997); Dvorkin et al. (1990a,b); Lampeka et al. (1989); Skopenko et al. (1990). For carbon dioxide capture, see: Kovbasyuk et al. (1997); Pavlishchuk et al. (2002); Nanda et al. (2006).

Experimental

Crystal data

(C₈H₁₈N₃O₂)₂[Cu₂(C₈H₁₅N₃O₂)₂(C₈H₁₇N₃O₂)₂] (C₉H₁₆N₃O₄)₂·2C₂H₃N
M_r = 1791.14
Triclinic, $[P \overline 1]$
a = 9.3077 (3) Å
b = 12.9458 (6) Å
c = 19.8381 (6) Å
= 107.875 (1)°
= 98.461 (2)°
= 92.718 (2)°
V = 2239.34 (14) Å³
Z = 1
Mo K radiation
= 0.55 mm^-1
T = 120 K
0.17 × 0.14 × 0.11 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995) T_min = 0.911, T_max = 0.944
32405 measured reflections
9811 independent reflections
7089 reflections with I > 2(I)
R_int = 0.074

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.147
S = 1.05
9811 reflections
545 parameters
H-atom parameters constrained
_max = 0.78 e Å^-3
_min = -0.70 e Å^-3

Table 1
Selected bond lengths (Å)

Cu1-N1	1.984 (2)
Cu1-N2	1.957 (2)
Cu1-N3	2.000 (2)
Cu1-N4	2.041 (2)
Cu1-O1ⁱ	2.441 (2)
Symmetry code: (i) -x+2, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H4OO2ⁱ	1.00	1.67	2.574 (3)	150
O6-H6OO1ⁱⁱ	0.91	1.71	2.613 (3)	174
N3-H3AO1ⁱⁱ	0.86	2.45	2.938 (3)	116
N3-H3BO3	0.90	2.16	2.978 (3)	151
N4-H4CO3	0.93	2.09	2.908 (3)	145
N4-H4DO1	0.92	2.47	2.967 (3)	115
N4-H4DN1ⁱⁱ	0.92	2.50	3.123 (3)	126
N7-H7DO5ⁱⁱⁱ	0.79	2.29	3.002 (3)	149
N7-H7DO5	0.79	2.60	3.109 (3)	123
N7-H7EO7ⁱⁱⁱ	0.87	1.84	2.705 (3)	172
N7-H7FO8^iv	1.05	1.82	2.859 (3)	169
N7-H7FO7^iv	1.05	2.43	2.981 (3)	112
N10-H10NN13^v	0.98	2.27	3.107 (5)	143
N11-H11NO7	0.90	1.95	2.773 (3)	151
O10-H10OO8^vi	0.86	1.77	2.626 (3)	169
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y, -z+1; (iii) -x+2, -y, -z; (iv) x+1, y, z; (v) -x+1, -y+1, -z; (vi) -x+1, -y, -z.

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2096 ).

Acknowledgements

This work was supported by the Russian Fund for Basic Research (grants11-03-00262 and 11-03-90417), the Federal Targeted Program Scientific and Scientific-Pedagogical Personnel of Innovative Russia in 2009-2013 (contract P1294 from 09/06/2010) and the State Fund for Fundamental Research of Ukraine (grant No. F40.3/041). Financial support from the Visby Program through the Swedish Institute is gratefully acknowledged.

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metal-organic compounds