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

In the title compound, [CuK(2)(C(3)N(2)O(3))(2)(H(2)O)(3)](n), the Cu(2+) atom is in a distorted square-pyramidal coordination geometry. Two N atoms belonging to the oxime groups and two O atoms belonging to the carboxyl-ate groups of two trans-disposed doubly deprotonated residues of 2-cyano-2-(hy-droxy-imino)-acetic acid make up the basal plane and the apical position is occupied by the water mol-ecule. 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 carboxyl-ate and the oxime O atoms and the nitrile N atoms of the ligand. The environments of the K(+) cations are complemented to octa- and nona-coordinated, by K-O contacts with H(2)O mol-ecules. 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 = 419.89

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.062

S = 1.09

3189 reflections

205 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.56 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036641/hp2047sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036641/hp2047Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CuK2(C3N2O3)2(H2O)3]	F(000) = 836
Mr = 419.89	Dx = 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

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

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(Fo2) + (0.028P)2 + 0.9392P] where P = (Fo2 + 2Fc2)/3
3189 reflections	(Δ/σ)max = 0.001
205 parameters	Δρmax = 0.56 e Å−3
4 restraints	Δρmin = −0.56 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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—N2iv	2.941 (2)	O2W—H22W	0.9250
K1—O1A	2.9795 (16)	O3W—K1v	2.8578 (16)
K1—O1iii	3.0011 (16)	O3W—H13W	0.8215
K2—O3W	2.7255 (17)	O3W—H23W	0.8882
K2—O2Wv	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—O3v	2.9795 (16)	N2—C1	1.146 (2)
K2—N2Avi	2.981 (2)	N2—K1viii	2.941 (2)
K2—O1W	2.9904 (17)	N2—K2ix	3.2763 (19)
K2—N2Aii	3.1018 (19)	N2A—C1A	1.151 (2)
K2—N2vii	3.2763 (19)	N2A—K2x	2.981 (2)
K2—N1	3.444 (2)	N2A—K2v	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)	O2Wv—K2—N2vii	68.12 (5)
O2—Cu1—N1A	95.20 (6)	O2A—K2—N2vii	80.79 (5)
O2A—Cu1—N1A	83.78 (6)	O1—K2—N2vii	69.31 (5)
O2—Cu1—N1	82.89 (6)	O3v—K2—N2vii	136.83 (4)
O2A—Cu1—N1	97.08 (6)	N2Avi—K2—N2vii	66.99 (5)
N1A—Cu1—N1	174.16 (6)	O1W—K2—N2vii	135.12 (4)
O2—Cu1—O1W	101.37 (6)	N2Aii—K2—N2vii	123.61 (5)
O2A—Cu1—O1W	89.19 (6)	O3W—K2—Cu1	136.80 (4)
N1A—Cu1—O1W	97.03 (6)	O2Wv—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)	O3v—K2—Cu1	75.44 (4)
N1A—Cu1—K2	118.52 (5)	N2Avi—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)	N2vii—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—K1v	43.95 (4)
N1—Cu1—K1iii	64.30 (5)	O2Wv—K2—K1v	41.71 (3)
O1W—Cu1—K1iii	122.53 (4)	O2A—K2—K1v	107.77 (4)
K2—Cu1—K1iii	69.53 (3)	O1—K2—K1v	167.26 (3)
O2W—K1—O2	69.00 (5)	O3v—K2—K1v	59.37 (4)
O2W—K1—O1Ai	65.22 (5)	N2Avi—K2—K1v	73.70 (5)
O2—K1—O1Ai	131.17 (4)	O1W—K2—K1v	112.48 (4)
O2W—K1—O3Wii	85.02 (5)	N2Aii—K2—K1v	122.80 (4)
O2—K1—O3Wii	95.09 (5)	N2vii—K2—K1v	98.98 (4)
O1Ai—K1—O3Wii	96.98 (5)	N1—K2—K1v	161.23 (3)
O2W—K1—O2Aiii	129.37 (5)	Cu1—K2—K1v	129.25 (3)
O2—K1—O2Aiii	68.90 (4)	O3W—K2—H21W	91.8
O1Ai—K1—O2Aiii	158.93 (4)	O2Wv—K2—H21W	104.1
O3Wii—K1—O2Aiii	72.05 (4)	O2A—K2—H21W	61.0
O2W—K1—N2iv	129.21 (5)	O1—K2—H21W	89.6
O2—K1—N2iv	154.70 (5)	O3v—K2—H21W	38.2
O1Ai—K1—N2iv	73.17 (5)	N2Avi—K2—H21W	151.5
O3Wii—K1—N2iv	72.16 (5)	O1W—K2—H21W	15.4
O2Aiii—K1—N2iv	86.19 (5)	N2Aii—K2—H21W	73.4
O2W—K1—O1A	81.80 (5)	N2vii—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)	K1v—K2—H21W	97.3
O2Aiii—K1—O1A	103.74 (4)	N1—O1—K2	104.00 (9)
N2iv—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)
N2iv—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)
N2iv—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)
N2iv—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—K1v	94.61 (5)
O2—K1—K2ii	76.44 (4)	K2—O3W—H13W	117.5
O1Ai—K1—K2ii	82.18 (4)	K1v—O3W—H13W	104.7
O3Wii—K1—K2ii	41.44 (3)	K2—O3W—H23W	121.2
O2Aiii—K1—K2ii	99.36 (4)	K1v—O3W—H23W	112.0
N2iv—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—O2Wv	85.40 (5)	Cu1—N1—K1iii	83.94 (5)
O3W—K2—O2A	140.56 (4)	O1—N1—K2	54.66 (8)
O2Wv—K2—O2A	75.60 (5)	C2—N1—K2	140.04 (11)
O3W—K2—O1	146.95 (4)	Cu1—N1—K2	82.25 (5)
O2Wv—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—O3v	68.49 (5)	O1A—N1A—Cu1	127.23 (12)
O2Wv—K2—O3v	72.48 (4)	C2A—N1A—Cu1	110.87 (11)
O2A—K2—O3v	72.90 (5)	C1—N2—K1viii	133.74 (14)
O1—K2—O3v	125.73 (4)	C1—N2—K2ix	122.50 (13)
O3W—K2—N2Avi	62.76 (5)	K1viii—N2—K2ix	87.14 (5)
O2Wv—K2—N2Avi	87.22 (5)	C1A—N2A—K2x	129.07 (13)
O2A—K2—N2Avi	147.35 (5)	C1A—N2A—K2v	138.19 (13)
O1—K2—N2Avi	104.84 (5)	K2x—N2A—K2v	91.29 (6)
O3v—K2—N2Avi	128.30 (5)	N2—C1—C2	178.38 (19)
O3W—K2—O1W	101.07 (5)	N2A—C1A—C2A	179.9 (3)
O2Wv—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)
O3v—K2—O1W	53.59 (4)	N1A—C2A—C1A	121.76 (15)
N2Avi—K2—O1W	151.06 (4)	N1A—C2A—C3A	116.05 (15)
O3W—K2—N2Aii	79.38 (5)	C1A—C2A—C3A	122.17 (15)
O2Wv—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)
O3v—K2—N2Aii	98.59 (5)	O3A—C3A—O2A	124.08 (15)
N2Avi—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—N2vii	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)

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···O3v	0.80	1.96	2.6910 (19)	151
O2W—H12W···O1xi	0.81	2.19	2.993 (2)	173
O2W—H22W···O3Aii	0.92	2.02	2.926 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11W⋯O3A i	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⋯O3A i	0.92	2.02	2.926 (2)	164

Symmetry codes: (i) ; (ii) ; (iii) .