Bis[bis­(1-oxo-2-pyrid­yl)­aminato]­copper(II) tetra­hydrate

Wang, L.-G.

doi:10.1107/S1600536809009453

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m420

doi:10.1107/S1600536809009453

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Bis[bis(1-oxo-2-pyridyl)aminato]copper(II) tetrahydrate

Liang-Gui Wang ^a ^*

^aCollege of Chemistry and Life Science, Lishui University, 323000 Lishui, Zhejiang, People's Republic of China
^*Correspondence e-mail: zjlswgl@126.com

(Received 5 March 2009; accepted 14 March 2009; online 19 March 2009)

In the title compound, [Cu(C₁₀H₈N₃O₂)₂]·4H₂O, the Cu^II ion has a distorted octahedral coordination formed by four O [Cu—O = 2.051 (3)–2.083 (4) Å] and two N [Cu—N = 1.985 (4) and 1.996 (4) Å] atoms from two tridentate bis(1-oxo-2-pyridyl)aminate ligands. In the two ligands, the pyridyl rings form dihedral angles of 21.0 (1) and 15.5 (1)°. The crystal packing exhibits an extensive network of O—H⋯O hydrogen bonds and π–π interactions proved by short distances of 3.650 (1) and 3.732 (2) Å between the centroids of pyridyl rings of neighbouring molecules.

Related literature

For general background, see Patra et al. (2004 ). For the crystal structures of related compounds, see: Kuang et al. (2006 ); Liu et al. (2007 , 2008 ).

Experimental

Crystal data

[Cu(C₁₀H₈N₃O₂)₂]·4H₂O
M_r = 539.99
Monoclinic, P 2₁ /c
a = 10.697 (3) Å
b = 17.607 (5) Å
c = 15.052 (3) Å
β = 127.136 (14)°
V = 2260.0 (10) Å³
Z = 4
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 298 K
0.29 × 0.22 × 0.18 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.755, T_max = 0.837
11476 measured reflections
4095 independent reflections
1752 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.159
S = 0.85
4095 reflections
340 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2WA⋯O3Wⁱⁱⁱ	0.85 (7)	2.01 (7)	2.800 (7)	156 (6)
O3W—H3WA⋯O4	0.85 (3)	1.99 (5)	2.808 (6)	163 (7)
O2W—H2WB⋯O3	0.84 (6)	2.01 (6)	2.848 (6)	172 (8)
O1W—H1WA⋯O1^iv	0.852 (10)	2.27 (4)	3.025 (6)	148 (7)
O1W—H1WB⋯O2Wⁱⁱ	0.86 (7)	1.96 (8)	2.755 (7)	153 (6)
O4W—H4WB⋯O4^v	0.84 (3)	2.17 (3)	2.951 (6)	154 (6)
Symmetry codes: (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x+1, y, z; (v) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009453/cv2529sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009453/cv2529Isup2.hkl

checkCIF report

Comment top

Bis(amidopyridine) ligands have been widely explored in coordination chemistry for building various novel structural architectures and functional solid materials. Besides their diverse coordination modes, amide groups of ligands have proved to be useful in self-assembly, since they give predictable patterns of hydrogen bonding that can add extra dimensionality and helicity to the supramolecular structures (Patra et al., 2004). The modified bis(1-oxo-2-pyridyl)aminato ligand and its complexes have been recently reported (Liu et al., 2007). In this paper, we report the synthesis and crystal structure of the title compound, (I).

The Cu^II atom in (I) (Fig.1) has a distorted octahedral coordination formed by two central N atoms and four O atoms of N-oxide groups from two bis(1-oxo-2-pyridyl)aminato ligands. This structure is very similar with [CuL₂]^.CH₃OH compound (Kuang et al., 2006). The average Cu—O bond length of 2.062 Å is close to the values observed in related complexes (Liu et al., 2008).

The crystal packing exhibits π–π interactions (Table 1) and an extensive network of O—H···O hydrogen bonds (Table 2).

Related literature top

For general background, see Patra et al. (2004). For the crystal structures of related compounds, see: Kuang et al. (2006); Liu et al. (2007, 2008).

Experimental top

Bis(1-oxo-2-pyridyl)aminato (0.062 g, 0.28 mmol), CuCl2 (0.024 g, 0.13 mmol), were added distilled water(12 mL), the mixture was heated for three hours under reflux. during the process stirring and influx were required. The resultant was kept at room temperature, three days later some single crystals of the size suitable for X-Ray diffraction measurement.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of (I) showing the atom-labelling scheme and 30% probability displacement ellipsoids.

Bis[bis(1-oxo-2-pyridyl)aminato]copper(II) tetrahydrate top

Crystal data top

[Cu(C₁₀H₈N₃O₂)₂]·4H₂O	F(000) = 1116
M_r = 539.99	D_x = 1.587 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1752 reflections
a = 10.697 (3) Å	θ = 2.1–25.3°
b = 17.607 (5) Å	µ = 1.03 mm⁻¹
c = 15.052 (3) Å	T = 298 K
β = 127.136 (14)°	Block, blue
V = 2260.0 (10) Å³	0.29 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	4095 independent reflections
Radiation source: fine-focus sealed tube	1752 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.076
ϕ and ω scans	θ_max = 25.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→12
T_min = 0.755, T_max = 0.837	k = −21→16
11476 measured reflections	l = −18→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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ²(F_o²) + (0.08P)² + 0.2094P] where P = (F_o² + 2F_c²)/3
4095 reflections	(Δ/σ)_max < 0.001
340 parameters	Δρ_max = 0.60 e Å⁻³
12 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Cu(C₁₀H₈N₃O₂)₂]·4H₂O	V = 2260.0 (10) Å³
M_r = 539.99	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.697 (3) Å	µ = 1.03 mm⁻¹
b = 17.607 (5) Å	T = 298 K
c = 15.052 (3) Å	0.29 × 0.22 × 0.18 mm
β = 127.136 (14)°

Data collection top

Bruker APEXII area-detector diffractometer	4095 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1752 reflections with I > 2σ(I)
T_min = 0.755, T_max = 0.837	R_int = 0.076
11476 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	12 restraints
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	Δρ_max = 0.60 e Å⁻³
4095 reflections	Δρ_min = −0.46 e Å⁻³
340 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.41065 (8)	0.62055 (4)	0.65999 (6)	0.0480 (3)
O4	0.5914 (4)	0.6883 (2)	0.6952 (3)	0.0476 (10)
O3	0.2092 (4)	0.5560 (2)	0.5640 (3)	0.0466 (10)
O2	0.5541 (4)	0.5283 (2)	0.7419 (3)	0.0511 (10)
O1	0.2746 (4)	0.7147 (2)	0.6342 (3)	0.0506 (10)
N5	0.3971 (5)	0.6065 (2)	0.5228 (3)	0.0366 (11)
N6	0.6029 (5)	0.6880 (2)	0.6100 (4)	0.0407 (11)
N4	0.1976 (4)	0.5258 (2)	0.4770 (3)	0.0355 (10)
N2	0.4349 (5)	0.6242 (3)	0.8015 (3)	0.0395 (11)
C18	0.6318 (6)	0.6939 (4)	0.4418 (5)	0.0567 (17)
H18	0.6409	0.6957	0.3841	0.068*
N3	0.6122 (5)	0.5311 (3)	0.8499 (4)	0.0471 (12)
N1	0.2569 (5)	0.7195 (3)	0.7140 (4)	0.0481 (13)
C15	0.2965 (5)	0.5512 (3)	0.4521 (4)	0.0369 (13)
C16	0.5016 (6)	0.6442 (3)	0.5173 (4)	0.0366 (14)
C14	0.2811 (6)	0.5125 (3)	0.3655 (4)	0.0423 (14)
H14	0.3488	0.5246	0.3483	0.051*
C6	0.5502 (6)	0.5803 (3)	0.8852 (5)	0.0435 (14)
C20	0.7135 (6)	0.7326 (3)	0.6203 (5)	0.0463 (15)
H20	0.7788	0.7616	0.6844	0.056*
C5	0.3413 (6)	0.6719 (3)	0.8065 (5)	0.0457 (15)
C11	0.0881 (6)	0.4723 (3)	0.4162 (5)	0.0448 (14)
H11	0.0214	0.4587	0.4338	0.054*
C12	0.0727 (6)	0.4377 (3)	0.3297 (5)	0.0499 (15)
H12	−0.0039	0.4010	0.2877	0.060*
C17	0.5199 (6)	0.6495 (3)	0.4335 (5)	0.0497 (16)
H17	0.4528	0.6216	0.3686	0.060*
C4	0.3090 (7)	0.6789 (4)	0.8835 (5)	0.0543 (17)
H4	0.3579	0.6463	0.9443	0.065*
C2	0.1304 (7)	0.7794 (4)	0.7821 (6)	0.065 (2)
H2	0.0616	0.8158	0.7745	0.078*
C3	0.2077 (7)	0.7324 (4)	0.8717 (6)	0.0638 (19)
H3	0.1914	0.7367	0.9257	0.077*
C13	0.1727 (7)	0.4582 (4)	0.3055 (5)	0.0541 (16)
H13	0.1656	0.4345	0.2473	0.065*
C19	0.7303 (7)	0.7357 (4)	0.5374 (5)	0.0594 (18)
H19	0.8080	0.7659	0.5455	0.071*
C1	0.1547 (6)	0.7728 (3)	0.7021 (5)	0.0592 (18)
H1	0.1016	0.8045	0.6401	0.071*
C10	0.7378 (7)	0.4870 (4)	0.9224 (6)	0.0613 (18)
H10	0.7791	0.4568	0.8951	0.074*
C9	0.8059 (8)	0.4848 (4)	1.0328 (6)	0.074 (2)
H9	0.8917	0.4537	1.0811	0.089*
C8	0.7422 (8)	0.5307 (4)	1.0702 (6)	0.075 (2)
H8	0.7840	0.5294	1.1452	0.091*
C7	0.6194 (7)	0.5779 (4)	0.9999 (5)	0.0548 (16)
H7	0.5807	0.6091	1.0281	0.066*
O1W	0.9650 (6)	0.6775 (3)	0.4134 (4)	0.0916 (16)
O2W	0.2615 (5)	0.4326 (3)	0.7051 (4)	0.0789 (14)
O3W	0.4779 (6)	0.8374 (3)	0.6629 (5)	0.0815 (14)
O4W	0.8955 (6)	0.8330 (4)	0.4159 (4)	0.0934 (16)
H2WA	0.354 (4)	0.415 (4)	0.744 (6)	0.140*
H2WB	0.250 (7)	0.472 (3)	0.669 (6)	0.140*
H3WB	0.384 (4)	0.847 (4)	0.638 (7)	0.140*
H1WA	1.029 (7)	0.684 (4)	0.4837 (14)	0.140*
H1WB	0.911 (8)	0.637 (3)	0.398 (6)	0.140*
H4WB	0.7981 (17)	0.832 (5)	0.365 (4)	0.140*
H4WA	0.952 (6)	0.817 (5)	0.398 (6)	0.140*
H3WA	0.499 (8)	0.7903 (12)	0.676 (7)	0.140*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0496 (4)	0.0564 (5)	0.0427 (5)	−0.0004 (4)	0.0303 (4)	−0.0027 (4)
O4	0.050 (2)	0.056 (3)	0.039 (2)	−0.010 (2)	0.0277 (19)	−0.005 (2)
O3	0.051 (2)	0.054 (3)	0.043 (2)	−0.0071 (19)	0.034 (2)	−0.011 (2)
O2	0.061 (2)	0.064 (3)	0.038 (2)	0.012 (2)	0.035 (2)	0.002 (2)
O1	0.056 (2)	0.060 (3)	0.040 (2)	0.010 (2)	0.032 (2)	0.002 (2)
N5	0.034 (2)	0.042 (3)	0.035 (3)	0.001 (2)	0.022 (2)	−0.001 (2)
N6	0.039 (3)	0.044 (3)	0.037 (3)	−0.001 (2)	0.022 (2)	0.004 (2)
N4	0.032 (2)	0.040 (3)	0.037 (3)	−0.001 (2)	0.022 (2)	−0.002 (2)
N2	0.044 (3)	0.047 (3)	0.034 (3)	0.004 (2)	0.027 (2)	−0.004 (2)
C18	0.046 (3)	0.081 (5)	0.048 (4)	0.004 (4)	0.031 (3)	0.013 (4)
N3	0.053 (3)	0.048 (3)	0.044 (3)	0.000 (3)	0.031 (3)	0.002 (3)
N1	0.037 (3)	0.062 (4)	0.041 (3)	−0.005 (3)	0.022 (2)	−0.017 (3)
C15	0.032 (3)	0.053 (4)	0.026 (3)	0.011 (3)	0.018 (3)	0.005 (3)
C16	0.029 (3)	0.053 (4)	0.026 (3)	0.004 (3)	0.016 (3)	0.003 (3)
C14	0.040 (3)	0.056 (4)	0.037 (3)	0.010 (3)	0.026 (3)	0.007 (3)
C6	0.052 (3)	0.051 (4)	0.040 (4)	−0.005 (3)	0.035 (3)	−0.002 (3)
C20	0.038 (3)	0.050 (4)	0.044 (4)	−0.008 (3)	0.021 (3)	0.001 (3)
C5	0.043 (3)	0.057 (4)	0.032 (3)	−0.012 (3)	0.020 (3)	−0.009 (3)
C11	0.041 (3)	0.047 (4)	0.050 (4)	−0.001 (3)	0.029 (3)	0.001 (3)
C12	0.048 (3)	0.045 (4)	0.049 (4)	−0.004 (3)	0.025 (3)	−0.010 (3)
C17	0.043 (3)	0.067 (4)	0.039 (4)	−0.004 (3)	0.024 (3)	−0.003 (3)
C4	0.054 (4)	0.075 (5)	0.043 (4)	−0.010 (4)	0.034 (3)	−0.014 (3)
C2	0.045 (4)	0.080 (5)	0.074 (5)	−0.006 (4)	0.037 (4)	−0.037 (4)
C3	0.054 (4)	0.094 (6)	0.057 (5)	−0.016 (4)	0.041 (4)	−0.025 (4)
C13	0.056 (4)	0.058 (4)	0.046 (4)	0.009 (4)	0.030 (3)	0.000 (3)
C19	0.044 (4)	0.070 (5)	0.061 (5)	−0.010 (3)	0.030 (4)	0.006 (4)
C1	0.039 (3)	0.056 (4)	0.064 (5)	0.001 (3)	0.021 (3)	−0.015 (3)
C10	0.054 (4)	0.061 (5)	0.065 (5)	0.009 (4)	0.033 (4)	0.009 (4)
C9	0.072 (4)	0.091 (6)	0.040 (4)	0.011 (4)	0.023 (4)	0.010 (4)
C8	0.082 (5)	0.081 (6)	0.044 (4)	−0.006 (5)	0.028 (4)	0.009 (4)
C7	0.064 (4)	0.063 (4)	0.041 (4)	−0.003 (4)	0.034 (3)	0.001 (3)
O1W	0.067 (3)	0.069 (4)	0.098 (4)	−0.002 (3)	0.029 (3)	0.017 (3)
O2W	0.087 (3)	0.069 (4)	0.082 (4)	−0.004 (3)	0.052 (3)	0.009 (3)
O3W	0.108 (4)	0.066 (3)	0.083 (4)	−0.003 (3)	0.064 (4)	−0.002 (3)
O4W	0.102 (4)	0.097 (4)	0.073 (4)	0.001 (4)	0.048 (3)	0.003 (3)

Geometric parameters (Å, º) top

Cu1—N2	1.985 (4)	C20—H20	0.9300
Cu1—N5	1.996 (4)	C5—C4	1.400 (7)
Cu1—O4	2.051 (3)	C11—C12	1.355 (7)
Cu1—O2	2.056 (4)	C11—H11	0.9300
Cu1—O3	2.064 (3)	C12—C13	1.371 (7)
Cu1—O1	2.083 (4)	C12—H12	0.9300
O4—N6	1.359 (5)	C17—H17	0.9300
O3—N4	1.348 (5)	C4—C3	1.364 (8)
O2—N3	1.347 (5)	C4—H4	0.9300
O1—N1	1.327 (5)	C2—C3	1.357 (9)
N5—C16	1.345 (6)	C2—C1	1.382 (8)
N5—C15	1.363 (6)	C2—H2	0.9300
N6—C20	1.350 (6)	C3—H3	0.9300
N6—C16	1.374 (6)	C13—H13	0.9300
N4—C11	1.342 (6)	C19—H19	0.9300
N4—C15	1.393 (6)	C1—H1	0.9300
N2—C5	1.343 (6)	C10—C9	1.354 (8)
N2—C6	1.353 (7)	C10—H10	0.9300
C18—C17	1.371 (7)	C9—C8	1.378 (9)
C18—C19	1.376 (8)	C9—H9	0.9300
C18—H18	0.9300	C8—C7	1.363 (8)
N3—C10	1.352 (7)	C8—H8	0.9300
N3—C6	1.377 (7)	C7—H7	0.9300
N1—C1	1.368 (7)	O1W—H1WA	0.852 (10)
N1—C5	1.393 (7)	O1W—H1WB	0.86 (7)
C15—C14	1.390 (7)	O2W—H2WA	0.85 (7)
C16—C17	1.391 (7)	O2W—H2WB	0.84 (6)
C14—C13	1.345 (7)	O3W—H3WB	0.85 (8)
C14—H14	0.9300	O3W—H3WA	0.85 (3)
C6—C7	1.410 (7)	O4W—H4WB	0.85 (8)
C20—C19	1.366 (7)	O4W—H4WA	0.85 (8)

Cg1···Cg3ⁱ	3.732 (2)	Cg2···Cg3ⁱⁱ	3.650 (1)

N2—Cu1—N5	174.15 (18)	N3—C6—C7	115.7 (5)
N2—Cu1—O4	102.22 (16)	N6—C20—C19	120.6 (5)
N5—Cu1—O4	78.90 (16)	N6—C20—H20	119.7
N2—Cu1—O2	79.40 (16)	C19—C20—H20	119.7
N5—Cu1—O2	94.82 (15)	N2—C5—N1	112.0 (5)
O4—Cu1—O2	93.35 (15)	N2—C5—C4	131.9 (6)
N2—Cu1—O3	100.02 (15)	N1—C5—C4	116.1 (5)
N5—Cu1—O3	79.34 (15)	N4—C11—C12	121.4 (5)
O4—Cu1—O3	157.50 (14)	N4—C11—H11	119.3
O2—Cu1—O3	94.08 (15)	C12—C11—H11	119.3
N2—Cu1—O1	78.36 (17)	C11—C12—C13	118.4 (5)
N5—Cu1—O1	107.41 (15)	C11—C12—H12	120.8
O4—Cu1—O1	91.64 (15)	C13—C12—H12	120.8
O2—Cu1—O1	157.76 (15)	C18—C17—C16	123.3 (5)
O3—Cu1—O1	89.47 (14)	C18—C17—H17	118.4
N6—O4—Cu1	111.2 (3)	C16—C17—H17	118.4
N4—O3—Cu1	110.0 (3)	C3—C4—C5	121.9 (6)
N3—O2—Cu1	109.1 (3)	C3—C4—H4	119.1
N1—O1—Cu1	110.3 (3)	C5—C4—H4	119.1
C16—N5—C15	126.8 (4)	C3—C2—C1	119.5 (6)
C16—N5—Cu1	117.3 (3)	C3—C2—H2	120.2
C15—N5—Cu1	115.2 (3)	C1—C2—H2	120.2
C20—N6—O4	117.4 (4)	C2—C3—C4	120.6 (6)
C20—N6—C16	122.8 (5)	C2—C3—H3	119.7
O4—N6—C16	119.8 (4)	C4—C3—H3	119.7
C11—N4—O3	118.1 (4)	C14—C13—C12	120.1 (6)
C11—N4—C15	122.3 (5)	C14—C13—H13	119.9
O3—N4—C15	119.7 (4)	C12—C13—H13	119.9
C5—N2—C6	126.6 (5)	C20—C19—C18	119.6 (6)
C5—N2—Cu1	117.5 (4)	C20—C19—H19	120.2
C6—N2—Cu1	115.8 (3)	C18—C19—H19	120.2
C17—C18—C19	118.4 (6)	N1—C1—C2	120.0 (6)
C17—C18—H18	120.8	N1—C1—H1	120.0
C19—C18—H18	120.8	C2—C1—H1	120.0
O2—N3—C10	117.5 (5)	N3—C10—C9	122.9 (6)
O2—N3—C6	120.7 (5)	N3—C10—H10	118.6
C10—N3—C6	121.7 (5)	C9—C10—H10	118.6
O1—N1—C1	117.6 (5)	C10—C9—C8	117.0 (7)
O1—N1—C5	120.5 (4)	C10—C9—H9	121.5
C1—N1—C5	121.9 (5)	C8—C9—H9	121.5
N5—C15—C14	132.4 (5)	C7—C8—C9	121.5 (6)
N5—C15—N4	112.9 (4)	C7—C8—H8	119.2
C14—C15—N4	114.5 (5)	C9—C8—H8	119.2
N5—C16—N6	112.9 (4)	C8—C7—C6	121.1 (6)
N5—C16—C17	131.8 (5)	C8—C7—H7	119.5
N6—C16—C17	115.3 (5)	C6—C7—H7	119.5
C13—C14—C15	123.1 (5)	H1WA—O1W—H1WB	111 (7)
C13—C14—H14	118.5	H2WA—O2W—H2WB	114 (8)
C15—C14—H14	118.5	H3WB—O3W—H3WA	112 (8)
N2—C6—N3	112.4 (5)	H4WB—O4W—H4WA	115 (3)
N2—C6—C7	131.8 (5)

Symmetry codes: (i) x, −y−1/2, z−3/2; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2WA···O3Wⁱⁱⁱ	0.85 (7)	2.01 (7)	2.800 (7)	156 (6)
O3W—H3WA···O4	0.85 (3)	1.99 (5)	2.808 (6)	163 (7)
O2W—H2WB···O3	0.84 (6)	2.01 (6)	2.848 (6)	172 (8)
O1W—H1WA···O1^iv	0.85 (1)	2.27 (4)	3.025 (6)	148 (7)
O1W—H1WB···O2Wⁱⁱ	0.86 (7)	1.96 (8)	2.755 (7)	153 (6)
O4W—H4WB···O4^v	0.84 (3)	2.17 (3)	2.951 (6)	154 (6)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₀H₈N₃O₂)₂]·4H₂O
M_r	539.99
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.697 (3), 17.607 (5), 15.052 (3)
β (°)	127.136 (14)
V (Å³)	2260.0 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.29 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.755, 0.837
No. of measured, independent and observed [I > 2σ(I)] reflections	11476, 4095, 1752
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.159, 0.85
No. of reflections	4095
No. of parameters	340
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.46

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).

Selected interatomic distances (Å) top

Cg1···Cg3ⁱ

3.732 (2)

Cg2···Cg3ⁱⁱ

3.650 (1)

Symmetry codes: (i) x, −y−1/2, z−3/2; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2WA···O3Wⁱⁱⁱ	0.85 (7)	2.01 (7)	2.800 (7)	156 (6)
O3W—H3WA···O4	0.85 (3)	1.99 (5)	2.808 (6)	163 (7)
O2W—H2WB···O3	0.84 (6)	2.01 (6)	2.848 (6)	172 (8)
O1W—H1WA···O1^iv	0.852 (10)	2.27 (4)	3.025 (6)	148 (7)
O1W—H1WB···O2Wⁱⁱ	0.86 (7)	1.96 (8)	2.755 (7)	153 (6)
O4W—H4WB···O4^v	0.84 (3)	2.17 (3)	2.951 (6)	154 (6)

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

Acknowledgements

The author is grateful to the Research Foundation of Lishui University (grant No. KZ08005) for financial support.

References

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