Poly[μ-aqua-diaquabis­[μ-2-cyano-2-(oxidoimino)­acetato]­copper(II)dipotassium]

Golenya, I.A.; Izotova, Y.A.; Usenko, N.I.; Kalibabchuk, V.A.; Kotova, N.V.

doi:10.1107/S1600536812036641

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Pages m1303-m1304

https://doi.org/10.1107/S1600536812036641

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Poly[μ-aqua-diaquabis[μ-2-cyano-2-(oxidoimino)acetato]copper(II)dipotassium]

Irina A. Golenya,^a Yulia A. Izotova,^b Natalia I. Usenko,^a Valentina A. Kalibabchuk ^c ^* and Natalia V. Kotova ^a

^aKiev National Taras Shevchenko University, Department of Chemistry, Volodymyrska Str. 64, 01601 Kiev, Ukraine, ^bDepartment of Chemistry, Saint-Petersburg State University, Universitetsky Pr. 26, 198504 Stary Petergof, Russian Federation, and ^cDepartment of General Chemistry, O. O. Bohomolets National Medical University, Shevchenko Blvd. 13, 01601 Kiev, Ukraine
^*Correspondence e-mail: kalibabchuk@ukr.net

(Received 18 August 2012; accepted 22 August 2012; online 26 September 2012)

In the title compound, [CuK₂(C₃N₂O₃)₂(H₂O)₃]_n, the Cu²⁺ atom is in a distorted square-pyramidal coordination geometry. Two N atoms belonging to the oxime groups and two O atoms belonging to the carboxylate groups of two trans-disposed doubly deprotonated residues of 2-cyano-2-(hydroxyimino)acetic acid make up the basal plane and the apical position is occupied by the water molecule. The neighboring Cu-containing moieties are linked into a three-dimensional framework by K—O and K—N contacts formed by two potassium cations with the carboxylate and the oxime O atoms and the nitrile N atoms of the ligand. The environments of the K⁺ cations are complemented to octa- and nonacoordinated, by K—O contacts with H₂O molecules. The crystal structure features O—H⋯O hydrogen bonds.

Related literature

For the use of mononuclear complexes in the preparation of polynuclear complexes, see: Kahn (1993 ); Goodwin et al. (2000 ); Krämer & Fritsky (2000 ); Fritsky et al. (2001 , 2003 ); Wörl et al. (2005 ). For the use of derivatives of 2-hydroxyiminocarboxylic acids and their derivatives as versatile ligands, see: Dvorkin et al. (1990a ,b ); Lampeka et al. (1989 ); Skopenko et al. (1990 ); Sachse et al. (2008 ); Fritsky et al. (1998 , 2006 ); Kanderal et al. (2005 ); Moroz et al. (2008 , 2010 , 2012 ). For metal complexes of 2-cyano-2-(hydroxyimino)acetic acid, see: Sliva et al. (1998 ); Mokhir et al. (2002 ); Eddings et al. (2004 ). For related structures, see: Duda et al. (1997 ); Fritsky et al. (2004 ); Onindo et al. (1995 ); Sliva et al. (1997 ); Świątek-Kozłowska et al. (2000 ); Kovbasyuk et al. (2004 ). For the synthesis of the ligand, see: Sliva et al. (1998).

Experimental

Crystal data

[CuK₂(C₃N₂O₃)₂(H₂O)₃]
M_r = 419.89
Monoclinic, P 2₁ /c
a = 8.767 (2) Å
b = 12.426 (3) Å
c = 13.159 (5) Å
β = 108.26 (3)°
V = 1361.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.27 mm⁻¹
T = 100 K
0.24 × 0.16 × 0.07 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.657, T_max = 0.859
9166 measured reflections
3189 independent reflections
3006 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.062
S = 1.09
3189 reflections
205 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11W⋯O3Aⁱ	0.89	1.85	2.7257 (19)	171
O1W—H21W⋯O3ⁱⁱ	0.80	1.96	2.6910 (19)	151
O2W—H12W⋯O1ⁱⁱⁱ	0.81	2.19	2.993 (2)	173
O2W—H22W⋯O3Aⁱ	0.92	2.02	2.926 (2)	164
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812036641/hp2047sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812036641/hp2047Isup2.hkl

checkCIF report

Comment top

Many reported mononuclear complexes of 3 d-metals contains vacant donor atoms or chelate centers, so that they can be considered as ligands for preparation of homo- and heteropolynuclear systems which are widely used in bioinorganic modeling, catalysis and in molecular magnetism (Kahn, 1993; Goodwin et al., 2000; Krämer et al., 2000; Fritsky et al., 2001; Fritsky et al., 2003; Wörl et al., 2005). Polydentate ligands containing oxime and carboxylic groups attract particular attention due to their potential for the bridging mode of coordination and mediation of strong magnetic exchange interactions between metal ions (Lampeka et al., 1989; Dvorkin et al., 1990a, 1990b; Skopenko et al., 1990; Sachse et al., 2008; Moroz et al., 2008, 2010, 2012) and for preparation of metal complexes with efficient stabilization of unusually high oxidation states of 3 d-metal ions like copper(III) and nickel(III) (Fritsky et al., 1998; Kanderal et al., 2005; Fritsky et al., 2006). 2-cyano-2-(hydroxyimino)acetic acid (aaco) is an efficient chelating ligand for Cu(II) and Ni(II) ions (Sliva et al., 1998; Mokhir et al., 2002). To date, only one heterometallic complex containing this ligand K₂[Pd(aaco-2H)₂].4H₂O has been structurally characterized (Eddings et al., 2004). Herein we report the second heterometallic complex based on 2-cyan-2-hydroxyiminoacetic acid.

The title compound, [K₂Cu(C₃N₂O₃)₂(H₂O)₃]_n, has an ionic structure containing 2- charged Cu(II)-centered complex anions, potassium cations and water molecules (Fig. 1). The Cu atom is in a distorted square-pyramidal geometry, defined by two N atoms belonging to the oxime groups and two O atoms belonging to the carboxylic groups of two trans-disposed doubly deprotonated residues of 2-cyano-2-(hydroxyimino)acetic acid. The apical position is occupied by the water molecule O1W which also serves as a bridge between Cu1 and K1 ions. The coordination bond lengths Cu—N and Cu—O (Table 1) are typical for square-pyramidal Cu(II) complexes with deprotonated oxime and carboxylate donors (Sliva et al., 1997; Kanderal et al., 2005). The bite angles around the central atom deviate from an ideal square-planar configuration [e.g. O2—Cu1—N1 = 82.89 (6)°], which is a consequence of the formation of five-membered chelate rings. The bond lengths C—O, N—O and C—N in the coordinated 2-oximinocarboxylate ligand are typical for copper(II) complexes with cyanoximes and carboxylates (Onindo et al., 1995; Duda et al., 1997; Fritsky et al., 2004;).

The potassium cations K1 and K2 are bound to the copper(II) complex anion in a chelate fashion via the oxime oxygen (O1A and O1, respectively) and the carboxylic oxygen (O2 and O2A, respectively) atoms. Such coordination of two potassium cations from the different side of the complex anion results in a closed metallamacrocylic framework. Both potassium cations also forms additional K—O and K—N contacts with the carboxylic and the oxime O atoms and the nitrile N atoms of the neighboring Cu complex anions thus uniting them in a three-dimensional framework (Fig. 2). The environments of K1 and K2 potassium cation are complemented to octa- and nona-coordinated, respectively, by K—O contacts with H₂O molecules. The K—O and K—N bond lengths are normal for potassium cations and close to those reported in the structures of the carboxylate and the oximate complexes (Fritsky et al., 1998; Świątek-Kozłowska et al., 2000; Kovbasyuk et al., 20040). The crystal structure involves intermolecular O—H···O hydrogen bonds where the water molecules act as donors, and the carboxylic and the oxime O atoms act as acceptors (Table 2).

Related literature top

For the use of mononuclear complexes in the preparation of polynuclear complexes, see: Kahn (1993); Goodwin et al. (2000); Krämer et al. (2000); Fritsky et al. (2001, 2003); Wörl et al. (2005). For the use of derivatives of 2-hydroxyiminocarboxylic acids and their derivatives as versatile ligands, see: Dvorkin et al. (1990a,b); Lampeka et al. (1989); Skopenko et al. (1990); Sachse et al. (2008); Fritsky et al. (1998, 2006); Kanderal et al. (2005); Moroz et al. (2008, 2010, 2012). For metal complexes of 2-cyano-2-(hydroxyimino)acetic acid, see: Sliva et al. (1998); Mokhir et al. (2002); Eddings et al. (2004). For related structures see: Duda et al. (1997); Fritsky et al. (2004); Onindo et al. (1995); Sliva et al. (1997); Świątek-Kozłowska et al. (2000); Kovbasyuk et al. (2004). For the synthesis of the ligand, see: Sliva et al. (1998).

Experimental top

Cu(NO₃)₂.3H₂O (0.242 g, 1 mmol) was dissolved in water (3 ml) and added to the methanolic solution (15 ml) of 2-cyano-2-(hydroxyimino)acetic acid (0.228 g, 2 mmol), synthesizsed according to Sliva et al., 1998). To the obtained mixture, aqueous solution of potassium hydroxide (1M, 4 ml) was added with vigorous stirring at room temperature. The obtained transparent solution was stirred 20 min. and then set aside for crystallization at ambient temperature. Bright brown crystals were separated by filtration after 72 h, washed with cold water (10 ml) and dried (yield 78%). Analysis calculated for C₆H₆Cu K₂N₄O₉: C 17.16, H 1.44, N 13.34%; found: C 17.10, H 1.53, N 13.42%.

Structure description top

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of compound (I), with displacement ellipsoids shown at the 50% probability level. H atoms are drawn as spheres of arbitrary radii. Symmetry codes: (i) -x, -y + 1, -z; (ii) -x + 1, y - 1/2, -z + 1/2; (iii) -x + 1, -y + 1, -z; (iv) x - 1, -y + 1/2, z - 1/2; (v) -x + 1, y + 1/2, -z + 1/2; (vi) x + 1, -y + 3/2, z + 1/2; (vii) -x + 2, y + 1/2, -z + 1/2.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are indicated by dashed lines.

Poly[µ-aqua-diaquabis[µ-2-cyano-2-(oxidoimino)acetato]copper(II)dipotassium] top

Crystal data top

[CuK₂(C₃N₂O₃)₂(H₂O)₃]	F(000) = 836
M_r = 419.89	D_x = 2.049 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3744 reflections
a = 8.767 (2) Å	θ = 1.0–27.5°
b = 12.426 (3) Å	µ = 2.27 mm⁻¹
c = 13.159 (5) Å	T = 100 K
β = 108.26 (3)°	Block, brown
V = 1361.3 (7) Å³	0.24 × 0.16 × 0.07 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	3189 independent reflections
Radiation source: fine-focus sealed tube	3006 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 28.4°, θ_min = 3.7°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −11→11
T_min = 0.657, T_max = 0.859	k = −15→15
9166 measured reflections	l = −14→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.028P)² + 0.9392P] where P = (F_o² + 2F_c²)/3
3189 reflections	(Δ/σ)_max = 0.001
205 parameters	Δρ_max = 0.56 e Å⁻³
4 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[CuK₂(C₃N₂O₃)₂(H₂O)₃]	V = 1361.3 (7) Å³
M_r = 419.89	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.767 (2) Å	µ = 2.27 mm⁻¹
b = 12.426 (3) Å	T = 100 K
c = 13.159 (5) Å	0.24 × 0.16 × 0.07 mm
β = 108.26 (3)°

Data collection top

Nonius KappaCCD area-detector diffractometer	3189 independent reflections
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	3006 reflections with I > 2σ(I)
T_min = 0.657, T_max = 0.859	R_int = 0.043
9166 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	4 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.09	Δρ_max = 0.56 e Å⁻³
3189 reflections	Δρ_min = −0.56 e Å⁻³
205 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Cu1	0.53009 (2)	0.529307 (15)	0.136932 (15)	0.00981 (7)
K1	0.10262 (4)	0.38634 (3)	−0.06404 (3)	0.01425 (9)
K2	0.86027 (5)	0.61378 (3)	0.38164 (3)	0.01645 (9)
O1	0.86577 (14)	0.45133 (10)	0.22512 (10)	0.0138 (2)
O1A	0.20044 (14)	0.60207 (10)	0.03346 (10)	0.0151 (2)
O2	0.41091 (14)	0.39928 (10)	0.08061 (10)	0.0139 (2)
O2A	0.65548 (14)	0.66325 (10)	0.16771 (9)	0.0117 (2)
O3	0.43256 (15)	0.22059 (10)	0.09720 (10)	0.0160 (3)
O3A	0.61938 (14)	0.84124 (10)	0.16679 (10)	0.0140 (2)
O1W	0.52488 (16)	0.52800 (10)	0.30436 (10)	0.0160 (3)
H11W	0.4781 (7)	0.4699 (8)	0.3201 (2)	0.024*
H21W	0.5029 (3)	0.5835 (8)	0.3278 (3)	0.024*
O2W	0.10231 (16)	0.33982 (12)	0.13939 (11)	0.0205 (3)
H12W	0.0333 (11)	0.3648 (4)	0.1612 (4)	0.031*
H22W	0.1900 (14)	0.3541 (3)	0.1987 (10)	0.031*
O3W	0.89136 (15)	0.65821 (11)	0.59001 (11)	0.0194 (3)
H13W	0.8132 (13)	0.6471 (2)	0.6103 (4)	0.029*
H23W	0.9754 (14)	0.6349 (4)	0.6428 (9)	0.029*
N1	0.71631 (17)	0.42739 (12)	0.18069 (11)	0.0111 (3)
N1A	0.34617 (17)	0.62774 (12)	0.07855 (11)	0.0113 (3)
N2	0.86325 (19)	0.16875 (13)	0.23004 (13)	0.0203 (3)
N2A	0.19141 (19)	0.88673 (13)	0.03683 (13)	0.0186 (3)
C1	0.7741 (2)	0.23825 (14)	0.20181 (13)	0.0125 (3)
C1A	0.2811 (2)	0.81670 (14)	0.06281 (13)	0.0128 (3)
C2	0.66627 (19)	0.32726 (14)	0.16742 (13)	0.0111 (3)
C2A	0.3926 (2)	0.72992 (14)	0.09515 (13)	0.0114 (3)
C3	0.4904 (2)	0.31178 (13)	0.11168 (13)	0.0114 (3)
C3A	0.5671 (2)	0.74813 (14)	0.14657 (13)	0.0109 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.00914 (11)	0.00802 (11)	0.01111 (11)	0.00006 (7)	0.00152 (8)	−0.00062 (7)
K1	0.01241 (17)	0.01672 (18)	0.01307 (17)	−0.00156 (13)	0.00320 (13)	−0.00110 (13)
K2	0.01638 (18)	0.01814 (19)	0.01222 (17)	0.00000 (14)	0.00070 (14)	−0.00195 (13)
O1	0.0092 (5)	0.0152 (6)	0.0157 (6)	−0.0015 (4)	0.0020 (5)	−0.0016 (5)
O1A	0.0103 (6)	0.0166 (6)	0.0168 (6)	−0.0026 (5)	0.0019 (5)	−0.0013 (5)
O2	0.0106 (5)	0.0111 (6)	0.0173 (6)	0.0003 (4)	0.0006 (5)	−0.0008 (4)
O2A	0.0103 (5)	0.0101 (5)	0.0142 (6)	0.0007 (4)	0.0029 (4)	0.0002 (4)
O3	0.0155 (6)	0.0104 (6)	0.0197 (6)	−0.0020 (5)	0.0021 (5)	−0.0001 (5)
O3A	0.0138 (6)	0.0112 (6)	0.0165 (6)	−0.0003 (5)	0.0037 (5)	−0.0016 (5)
O1W	0.0230 (7)	0.0095 (6)	0.0175 (6)	−0.0016 (5)	0.0093 (5)	−0.0011 (4)
O2W	0.0131 (6)	0.0311 (7)	0.0163 (6)	0.0019 (5)	0.0033 (5)	−0.0007 (5)
O3W	0.0145 (6)	0.0269 (7)	0.0169 (6)	0.0023 (5)	0.0049 (5)	0.0017 (5)
N1	0.0110 (6)	0.0134 (7)	0.0088 (6)	0.0010 (5)	0.0030 (5)	−0.0006 (5)
N1A	0.0103 (6)	0.0138 (7)	0.0098 (6)	−0.0007 (5)	0.0034 (5)	−0.0002 (5)
N2	0.0195 (8)	0.0178 (8)	0.0200 (8)	0.0028 (6)	0.0010 (6)	0.0000 (6)
N2A	0.0147 (7)	0.0180 (8)	0.0212 (8)	0.0026 (6)	0.0029 (6)	0.0006 (6)
C1	0.0118 (7)	0.0140 (8)	0.0103 (7)	−0.0018 (6)	0.0015 (6)	−0.0009 (6)
C1A	0.0120 (7)	0.0149 (8)	0.0110 (7)	−0.0017 (6)	0.0028 (6)	−0.0017 (6)
C2	0.0115 (7)	0.0123 (7)	0.0093 (7)	0.0009 (6)	0.0030 (6)	0.0000 (6)
C2A	0.0117 (8)	0.0131 (8)	0.0094 (7)	0.0021 (6)	0.0036 (6)	0.0000 (6)
C3	0.0111 (7)	0.0140 (8)	0.0085 (7)	−0.0004 (6)	0.0023 (6)	0.0006 (6)
C3A	0.0112 (7)	0.0139 (8)	0.0080 (7)	0.0014 (6)	0.0038 (6)	0.0008 (6)

Geometric parameters (Å, º) top

Cu1—O2	1.9407 (14)	O2—C3	1.287 (2)
Cu1—O2A	1.9656 (14)	O2A—C3A	1.287 (2)
Cu1—N1A	1.9774 (16)	O2A—K1ⁱⁱⁱ	2.9244 (15)
Cu1—N1	2.0029 (16)	O3—C3	1.231 (2)
Cu1—O1W	2.2181 (15)	O3—K2ⁱⁱ	2.9795 (16)
K1—O2W	2.7395 (17)	O3A—C3A	1.242 (2)
K1—O2	2.7803 (16)	O1W—H11W	0.8863
K1—O1Aⁱ	2.8128 (14)	O1W—H21W	0.8027
K1—O3Wⁱⁱ	2.8578 (16)	O2W—K2ⁱⁱ	2.8513 (17)
K1—O2Aⁱⁱⁱ	2.9244 (15)	O2W—H12W	0.8088
K1—N2^iv	2.941 (2)	O2W—H22W	0.9250
K1—O1A	2.9795 (16)	O3W—K1^v	2.8578 (16)
K1—O1ⁱⁱⁱ	3.0011 (16)	O3W—H13W	0.8215
K2—O3W	2.7255 (17)	O3W—H23W	0.8882
K2—O2W^v	2.8513 (17)	N1—C2	1.313 (2)
K2—O2A	2.8911 (18)	N1—K1ⁱⁱⁱ	3.4294 (18)
K2—O1	2.8951 (16)	N1A—C2A	1.330 (2)
K2—O3^v	2.9795 (16)	N2—C1	1.146 (2)
K2—N2A^vi	2.981 (2)	N2—K1^viii	2.941 (2)
K2—O1W	2.9904 (17)	N2—K2^ix	3.2763 (19)
K2—N2Aⁱⁱ	3.1018 (19)	N2A—C1A	1.151 (2)
K2—N2^vii	3.2763 (19)	N2A—K2^x	2.981 (2)
K2—N1	3.444 (2)	N2A—K2^v	3.1018 (18)
O1—N1	1.2911 (19)	C1—C2	1.433 (2)
O1—K1ⁱⁱⁱ	3.0011 (16)	C1A—C2A	1.428 (2)
O1A—N1A	1.2692 (19)	C2—C3	1.498 (2)
O1A—K1ⁱ	2.8128 (14)	C2A—C3A	1.483 (2)

O2—Cu1—O2A	169.44 (5)	O2W^v—K2—N2^vii	68.12 (5)
O2—Cu1—N1A	95.20 (6)	O2A—K2—N2^vii	80.79 (5)
O2A—Cu1—N1A	83.78 (6)	O1—K2—N2^vii	69.31 (5)
O2—Cu1—N1	82.89 (6)	O3^v—K2—N2^vii	136.83 (4)
O2A—Cu1—N1	97.08 (6)	N2A^vi—K2—N2^vii	66.99 (5)
N1A—Cu1—N1	174.16 (6)	O1W—K2—N2^vii	135.12 (4)
O2—Cu1—O1W	101.37 (6)	N2Aⁱⁱ—K2—N2^vii	123.61 (5)
O2A—Cu1—O1W	89.19 (6)	O3W—K2—Cu1	136.80 (4)
N1A—Cu1—O1W	97.03 (6)	O2W^v—K2—Cu1	105.92 (4)
N1—Cu1—O1W	88.76 (6)	O2A—K2—Cu1	31.24 (3)
O2—Cu1—K2	137.80 (4)	O1—K2—Cu1	51.18 (3)
O2A—Cu1—K2	49.71 (4)	O3^v—K2—Cu1	75.44 (4)
N1A—Cu1—K2	118.52 (5)	N2A^vi—K2—Cu1	156.01 (4)
N1—Cu1—K2	65.73 (5)	O1W—K2—Cu1	36.34 (3)
O1W—Cu1—K2	53.03 (4)	N2Aⁱⁱ—K2—Cu1	83.40 (5)
O2—Cu1—K1ⁱⁱⁱ	122.19 (4)	N2^vii—K2—Cu1	98.86 (4)
O2A—Cu1—K1ⁱⁱⁱ	49.64 (4)	N1—K2—Cu1	32.02 (3)
N1A—Cu1—K1ⁱⁱⁱ	112.66 (5)	O3W—K2—K1^v	43.95 (4)
N1—Cu1—K1ⁱⁱⁱ	64.30 (5)	O2W^v—K2—K1^v	41.71 (3)
O1W—Cu1—K1ⁱⁱⁱ	122.53 (4)	O2A—K2—K1^v	107.77 (4)
K2—Cu1—K1ⁱⁱⁱ	69.53 (3)	O1—K2—K1^v	167.26 (3)
O2W—K1—O2	69.00 (5)	O3^v—K2—K1^v	59.37 (4)
O2W—K1—O1Aⁱ	65.22 (5)	N2A^vi—K2—K1^v	73.70 (5)
O2—K1—O1Aⁱ	131.17 (4)	O1W—K2—K1^v	112.48 (4)
O2W—K1—O3Wⁱⁱ	85.02 (5)	N2Aⁱⁱ—K2—K1^v	122.80 (4)
O2—K1—O3Wⁱⁱ	95.09 (5)	N2^vii—K2—K1^v	98.98 (4)
O1Aⁱ—K1—O3Wⁱⁱ	96.98 (5)	N1—K2—K1^v	161.23 (3)
O2W—K1—O2Aⁱⁱⁱ	129.37 (5)	Cu1—K2—K1^v	129.25 (3)
O2—K1—O2Aⁱⁱⁱ	68.90 (4)	O3W—K2—H21W	91.8
O1Aⁱ—K1—O2Aⁱⁱⁱ	158.93 (4)	O2W^v—K2—H21W	104.1
O3Wⁱⁱ—K1—O2Aⁱⁱⁱ	72.05 (4)	O2A—K2—H21W	61.0
O2W—K1—N2^iv	129.21 (5)	O1—K2—H21W	89.6
O2—K1—N2^iv	154.70 (5)	O3^v—K2—H21W	38.2
O1Aⁱ—K1—N2^iv	73.17 (5)	N2A^vi—K2—H21W	151.5
O3Wⁱⁱ—K1—N2^iv	72.16 (5)	O1W—K2—H21W	15.4
O2Aⁱⁱⁱ—K1—N2^iv	86.19 (5)	N2Aⁱⁱ—K2—H21W	73.4
O2W—K1—O1A	81.80 (5)	N2^vii—K2—H21W	141.4
O2—K1—O1A	64.30 (5)	N1—K2—H21W	68.4
O1Aⁱ—K1—O1A	92.85 (4)	Cu1—K2—H21W	45.2
O3Wⁱⁱ—K1—O1A	158.48 (4)	K1^v—K2—H21W	97.3
O2Aⁱⁱⁱ—K1—O1A	103.74 (4)	N1—O1—K2	104.00 (9)
N2^iv—K1—O1A	129.20 (5)	N1—O1—K1ⁱⁱⁱ	98.06 (9)
O2W—K1—O1ⁱⁱⁱ	149.39 (4)	K2—O1—K1ⁱⁱⁱ	93.42 (5)
O2—K1—O1ⁱⁱⁱ	99.18 (5)	N1A—O1A—K1ⁱ	141.06 (10)
O1Aⁱ—K1—O1ⁱⁱⁱ	111.53 (5)	N1A—O1A—K1	122.63 (10)
O3Wⁱⁱ—K1—O1ⁱⁱⁱ	124.96 (4)	K1ⁱ—O1A—K1	87.15 (4)
O2Aⁱⁱⁱ—K1—O1ⁱⁱⁱ	64.61 (4)	C3—O2—Cu1	114.14 (11)
N2^iv—K1—O1ⁱⁱⁱ	72.71 (5)	C3—O2—K1	118.81 (10)
O1A—K1—O1ⁱⁱⁱ	67.77 (4)	Cu1—O2—K1	126.95 (6)
O2W—K1—Cu1ⁱⁱⁱ	124.58 (4)	C3A—O2A—Cu1	112.93 (11)
O2—K1—Cu1ⁱⁱⁱ	55.64 (4)	C3A—O2A—K2	122.22 (10)
O1Aⁱ—K1—Cu1ⁱⁱⁱ	159.87 (3)	Cu1—O2A—K2	99.04 (6)
O3Wⁱⁱ—K1—Cu1ⁱⁱⁱ	101.26 (4)	C3A—O2A—K1ⁱⁱⁱ	123.20 (10)
O2Aⁱⁱⁱ—K1—Cu1ⁱⁱⁱ	30.81 (3)	Cu1—O2A—K1ⁱⁱⁱ	99.55 (5)
N2^iv—K1—Cu1ⁱⁱⁱ	104.42 (4)	K2—O2A—K1ⁱⁱⁱ	95.14 (5)
O1A—K1—Cu1ⁱⁱⁱ	72.96 (4)	C3—O3—K2ⁱⁱ	136.08 (11)
O1ⁱⁱⁱ—K1—Cu1ⁱⁱⁱ	50.26 (3)	Cu1—O1W—K2	90.63 (5)
N1ⁱⁱⁱ—K1—Cu1ⁱⁱⁱ	31.75 (3)	Cu1—O1W—H11W	113.2
O2W—K1—K1ⁱ	66.33 (4)	K2—O1W—H11W	133.5
O2—K1—K1ⁱ	98.05 (4)	Cu1—O1W—H21W	117.2
O1Aⁱ—K1—K1ⁱ	48.16 (3)	K2—O1W—H21W	83.8
O3Wⁱⁱ—K1—K1ⁱ	141.22 (3)	H11W—O1W—H21W	115.1
O2Aⁱⁱⁱ—K1—K1ⁱ	146.54 (3)	K1—O2W—K2ⁱⁱ	94.45 (5)
N2^iv—K1—K1ⁱ	105.52 (5)	K1—O2W—H12W	119.7
O1A—K1—K1ⁱ	44.69 (3)	K2ⁱⁱ—O2W—H12W	122.3
O1ⁱⁱⁱ—K1—K1ⁱ	88.64 (4)	K1—O2W—H22W	122.0
N1ⁱⁱⁱ—K1—K1ⁱ	92.55 (3)	K2ⁱⁱ—O2W—H22W	100.4
Cu1ⁱⁱⁱ—K1—K1ⁱ	116.27 (3)	H12W—O2W—H22W	98.2
O2W—K1—K2ⁱⁱ	43.83 (4)	K2—O3W—K1^v	94.61 (5)
O2—K1—K2ⁱⁱ	76.44 (4)	K2—O3W—H13W	117.5
O1Aⁱ—K1—K2ⁱⁱ	82.18 (4)	K1^v—O3W—H13W	104.7
O3Wⁱⁱ—K1—K2ⁱⁱ	41.44 (3)	K2—O3W—H23W	121.2
O2Aⁱⁱⁱ—K1—K2ⁱⁱ	99.36 (4)	K1^v—O3W—H23W	112.0
N2^iv—K1—K2ⁱⁱ	104.45 (5)	H13W—O3W—H23W	105.3
O1A—K1—K2ⁱⁱ	122.09 (4)	O1—N1—C2	121.88 (14)
O1ⁱⁱⁱ—K1—K2ⁱⁱ	163.67 (3)	O1—N1—Cu1	127.20 (11)
N1ⁱⁱⁱ—K1—K2ⁱⁱ	148.83 (3)	C2—N1—Cu1	110.65 (11)
Cu1ⁱⁱⁱ—K1—K2ⁱⁱ	117.31 (3)	O1—N1—K1ⁱⁱⁱ	60.05 (8)
K1ⁱ—K1—K2ⁱⁱ	107.48 (3)	C2—N1—K1ⁱⁱⁱ	139.68 (11)
O3W—K2—O2W^v	85.40 (5)	Cu1—N1—K1ⁱⁱⁱ	83.94 (5)
O3W—K2—O2A	140.56 (4)	O1—N1—K2	54.66 (8)
O2W^v—K2—O2A	75.60 (5)	C2—N1—K2	140.04 (11)
O3W—K2—O1	146.95 (4)	Cu1—N1—K2	82.25 (5)
O2W^v—K2—O1	126.14 (4)	K1ⁱⁱⁱ—N1—K2	77.30 (4)
O2A—K2—O1	66.37 (5)	O1A—N1A—C2A	121.87 (15)
O3W—K2—O3^v	68.49 (5)	O1A—N1A—Cu1	127.23 (12)
O2W^v—K2—O3^v	72.48 (4)	C2A—N1A—Cu1	110.87 (11)
O2A—K2—O3^v	72.90 (5)	C1—N2—K1^viii	133.74 (14)
O1—K2—O3^v	125.73 (4)	C1—N2—K2^ix	122.50 (13)
O3W—K2—N2A^vi	62.76 (5)	K1^viii—N2—K2^ix	87.14 (5)
O2W^v—K2—N2A^vi	87.22 (5)	C1A—N2A—K2^x	129.07 (13)
O2A—K2—N2A^vi	147.35 (5)	C1A—N2A—K2^v	138.19 (13)
O1—K2—N2A^vi	104.84 (5)	K2^x—N2A—K2^v	91.29 (6)
O3^v—K2—N2A^vi	128.30 (5)	N2—C1—C2	178.38 (19)
O3W—K2—O1W	101.07 (5)	N2A—C1A—C2A	179.9 (3)
O2W^v—K2—O1W	116.68 (5)	N1—C2—C1	121.99 (15)
O2A—K2—O1W	60.02 (4)	N1—C2—C3	115.90 (15)
O1—K2—O1W	75.13 (5)	C1—C2—C3	122.10 (15)
O3^v—K2—O1W	53.59 (4)	N1A—C2A—C1A	121.76 (15)
N2A^vi—K2—O1W	151.06 (4)	N1A—C2A—C3A	116.05 (15)
O3W—K2—N2Aⁱⁱ	79.38 (5)	C1A—C2A—C3A	122.17 (15)
O2W^v—K2—N2Aⁱⁱ	164.43 (4)	O3—C3—O2	124.94 (15)
O2A—K2—N2Aⁱⁱ	114.63 (5)	O3—C3—C2	120.30 (15)
O1—K2—N2Aⁱⁱ	69.43 (5)	O2—C3—C2	114.75 (15)
O3^v—K2—N2Aⁱⁱ	98.59 (5)	O3A—C3A—O2A	124.08 (15)
N2A^vi—K2—N2Aⁱⁱ	88.71 (6)	O3A—C3A—C2A	119.89 (15)
O1W—K2—N2Aⁱⁱ	63.82 (5)	O2A—C3A—C2A	116.03 (15)
O3W—K2—N2^vii	123.65 (5)

O2—Cu1—O2A—C3A	90.4 (3)	O1—N1—C2—C3	−178.21 (13)
N1A—Cu1—O2A—C3A	5.42 (11)	Cu1—N1—C2—C3	7.32 (17)
N1—Cu1—O2A—C3A	179.61 (11)	O1A—N1A—C2A—C1A	−0.2 (2)
O1W—Cu1—O2A—C3A	−91.74 (11)	Cu1—N1A—C2A—C1A	−178.39 (12)
O2—Cu1—N1—O1	175.68 (13)	O1A—N1A—C2A—C3A	−178.72 (14)
O2A—Cu1—N1—O1	6.32 (14)	Cu1—O2—C3—O3	170.18 (14)
O1W—Cu1—N1—O1	−82.70 (13)	Cu1—O2—C3—C2	−10.95 (18)
O2—Cu1—N1—C2	−10.22 (11)	N1—C2—C3—O3	−178.94 (15)
O2A—Cu1—N1—C2	−179.58 (11)	C1—C2—C3—O3	2.5 (2)
O1W—Cu1—N1—C2	91.39 (12)	N1—C2—C3—O2	2.1 (2)
O2—Cu1—N1A—O1A	7.99 (14)	C1—C2—C3—O2	−176.39 (15)
O2A—Cu1—N1A—O1A	177.43 (14)	Cu1—O2A—C3A—O3A	174.67 (13)
O1W—Cu1—N1A—O1A	−94.17 (14)	Cu1—O2A—C3A—C2A	−5.14 (17)
O2—Cu1—N1A—C2A	−173.99 (11)	N1A—C2A—C3A—O3A	−178.48 (14)
O2A—Cu1—N1A—C2A	−4.55 (11)	C1A—C2A—C3A—O3A	3.0 (2)
O1W—Cu1—N1A—C2A	83.86 (12)	N1A—C2A—C3A—O2A	1.3 (2)
O1—N1—C2—C1	0.3 (2)	C1A—C2A—C3A—O2A	−177.14 (14)
Cu1—N1—C2—C1	−174.16 (12)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z; (iv) x−1, −y+1/2, z−1/2; (v) −x+1, y+1/2, −z+1/2; (vi) x+1, −y+3/2, z+1/2; (vii) −x+2, y+1/2, −z+1/2; (viii) x+1, −y+1/2, z+1/2; (ix) −x+2, y−1/2, −z+1/2; (x) x−1, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O3Aⁱⁱ	0.89	1.85	2.7257 (19)	171
O1W—H21W···O3^v	0.80	1.96	2.6910 (19)	151
O2W—H12W···O1^xi	0.81	2.19	2.993 (2)	173
O2W—H22W···O3Aⁱⁱ	0.92	2.02	2.926 (2)	164

Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (v) −x+1, y+1/2, −z+1/2; (xi) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[CuK₂(C₃N₂O₃)₂(H₂O)₃]
M_r	419.89
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.767 (2), 12.426 (3), 13.159 (5)
β (°)	108.26 (3)
V (Å³)	1361.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.27
Crystal size (mm)	0.24 × 0.16 × 0.07

Data collection
Diffractometer	Nonius KappaCCD area-detector
Absorption correction	Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.657, 0.859
No. of measured, independent and observed [I > 2σ(I)] reflections	9166, 3189, 3006
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.062, 1.09
No. of reflections	3189
No. of parameters	205
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.56

Computer programs: COLLECT (Nonius, 2000), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O3Aⁱ	0.89	1.85	2.7257 (19)	171.4
O1W—H21W···O3ⁱⁱ	0.80	1.96	2.6910 (19)	150.8
O2W—H12W···O1ⁱⁱⁱ	0.81	2.19	2.993 (2)	172.6
O2W—H22W···O3Aⁱ	0.92	2.02	2.926 (2)	164.3

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x−1, y, z.

Acknowledgements

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

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Poly[μ-aqua-di­aquabis­[μ-2-cyano-2-(oxido­imino)­acetato]­copper(II)dipotassium]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Poly[μ-aqua-diaquabis[μ-2-cyano-2-(oxidoimino)acetato]copper(II)dipotassium]