Bis(3,5-dimethyl-1H-pyrazole-κN2)(pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)copper(II)

Lin, Y.-Y.; Yu, Y.-P.; Liu, B.-X.; Zhang, L.-J.

doi:10.1107/S1600536809004577

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page m279

doi:10.1107/S1600536809004577

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Bis(3,5-dimethyl-1H-pyrazole-κN²)(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)copper(II)

Yuan-Yuan Lin,^a Yan-Ping Yu,^a Bing-Xin Liu ^a ^* and Liang-Jun Zhang ^b

^aDepartment of Chemistry, Shanghai University, Shanghai 200444, People's Republic of China, and ^bDepartment of Petroleum and Chemical Industry, Guangxi Vocational and Technical Institute of Industry, People's Republic of China
^*Correspondence e-mail: r5744011@yahoo.com.cn

(Received 12 October 2008; accepted 9 February 2009; online 18 February 2009)

In the crystal structure of the title compound, [Cu(C₇H₃NO₄)(C₅H₈N₂)₂], the Cu^II cation assumes a distorted trigonal–bipyramidal coordination geometry formed by a pyridine-2,6-dicarboxylate dianion and two 3,5-dimethyl-1H-pyrazole molecules. N—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For general background, see: Haanstra et al. (1990 ); Mukherjee (2000 ).

Experimental

Crystal data

[Cu(C₇H₃NO₄)(C₅H₈N₂)₂]
M_r = 420.91
Triclinic, $[P \overline 1]$
a = 8.4572 (12) Å
b = 8.5083 (12) Å
c = 13.942 (2) Å
α = 72.986 (2)°
β = 85.500 (2)°
γ = 66.760 (2)°
V = 880.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.28 mm⁻¹
T = 295 K
0.23 × 0.15 × 0.13 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.775, T_max = 0.845
4570 measured reflections
3036 independent reflections
2497 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.106
S = 1.05
3036 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu—N11	1.917 (3)
Cu—N21	2.172 (3)
Cu—N31	1.994 (3)
Cu—O11	2.025 (2)
Cu—O13	2.006 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N22—H22A⋯O14ⁱ	0.86	2.10	2.888 (4)	151
N32—H32A⋯O12ⁱⁱ	0.86	2.06	2.860 (4)	155
Symmetry codes: (i) x, y+1, z; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004577/xu2458sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004577/xu2458Isup2.hkl

checkCIF report

Comment top

Complexes with pyrazole-based ligands are a frequent subject of chemical investigations giving an opportunity for a better understanding the relationship between the structure and the activity of the active site of metalloproteins (Haanstra et al., 1990). Nowadays, attention is paid to the design of various pyrazole ligands with special structural properties to fulfill the specific stereochemical requirements of a particular metal-binding site (Mukherjee, 2000). In our systematic studies on transition metal complexes with the pyrazole derivatives, the title compound was prepared and its X-ray structure is presented here.

The molecular structure of the title compound is shown in Fig. 1. The compound assumes a distorted triangular bipyramid coordination geometry (Table 1), formed by a pyridine-2,6-dicarboxylate dianion and two 3,5-dimethyl-1-H-pyrazole molecules. Tridentate ligand pyridine-2,6-dicarboxylate dianion chelates to the Cu atom by a N atom of pyridine ring and two O atoms of carboxyl groups with a meridional configuration. Monodentate ligand 3,5-dimethyl-1-H-pyrazole coordinated to the Cu atom by N atoms of pyrazole rings with the 1.917 (3) Å and 1.994 (3) Å of Cu—N bound distance. The adjacent molecules are linked together via N—H···O hydrogen bonding (Table 2) between carboxy groups of pyridine-2,6-dicarboxylate dianion and uncoordinated N atom of 3,5-dimethyl-1-H-pyrazoleto, forming the supra-molecular structure (Fig. 2).

Related literature top

For general background, see: Haanstra et al. (1990); Mukherjee (2000).

Experimental top

An ethanol–water solution (1:1, 20 ml) containing 1-carboxamide-3,5-dimethylpyrazole (0.14 g, 1 mmol) and CuCl₂.2H₂O (0.17 g, 1 mmol) was mixed with an aqueous solution (10 ml) of pyridine-2,3-dicarboxylic acid (0.17 g, 1 mmol) and NaOH (0.08 g, 2 mmol). The mixture was refluxed for 6 h. After cooling to room temperature the solution was filtered. Single crystals were obtained from the filtrate after 3 d.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids.
	Fig. 2. The unit cell packing diagram showing hydrogen bonding (dashed lines).

Bis(3,5-dimethyl-1H-pyrazole-κN²)(pyridine-2,6- dicarboxylato-κ³O²,N,O⁶)copper(II) top

Crystal data top

[Cu(C₇H₃NO₄)(C₅H₈N₂)₂]	Z = 2
M_r = 420.91	F(000) = 434
Triclinic, P1	D_x = 1.587 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4572 (12) Å	Cell parameters from 2980 reflections
b = 8.5083 (12) Å	θ = 2.0–25.0°
c = 13.942 (2) Å	µ = 1.28 mm⁻¹
α = 72.986 (2)°	T = 295 K
β = 85.500 (2)°	Prism, blue
γ = 66.760 (2)°	0.23 × 0.15 × 0.13 mm
V = 880.7 (2) Å³

Data collection top

Bruker APEX CCD diffractometer	3036 independent reflections
Radiation source: fine-focus sealed tube	2497 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→10
T_min = 0.775, T_max = 0.845	k = −8→10
4570 measured reflections	l = −16→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.044P)² + 0.8468P] where P = (F_o² + 2F_c²)/3
3036 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Cu(C₇H₃NO₄)(C₅H₈N₂)₂]	γ = 66.760 (2)°
M_r = 420.91	V = 880.7 (2) Å³
Triclinic, P1	Z = 2
a = 8.4572 (12) Å	Mo Kα radiation
b = 8.5083 (12) Å	µ = 1.28 mm⁻¹
c = 13.942 (2) Å	T = 295 K
α = 72.986 (2)°	0.23 × 0.15 × 0.13 mm
β = 85.500 (2)°

Data collection top

Bruker APEX CCD diffractometer	3036 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2497 reflections with I > 2σ(I)
T_min = 0.775, T_max = 0.845	R_int = 0.020
4570 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.05	Δρ_max = 0.67 e Å⁻³
3036 reflections	Δρ_min = −0.55 e Å⁻³
248 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
Cu	0.48595 (5)	0.08560 (6)	0.27695 (4)	0.03571 (17)
O11	0.6674 (3)	0.1852 (3)	0.2773 (2)	0.0441 (7)
O12	0.9462 (3)	0.1267 (4)	0.2534 (2)	0.0532 (8)
O13	0.3807 (3)	−0.0884 (3)	0.2770 (2)	0.0422 (6)
O14	0.4427 (4)	−0.3530 (4)	0.2516 (2)	0.0509 (7)
N11	0.6858 (3)	−0.1038 (4)	0.2513 (2)	0.0293 (6)
N21	0.3623 (4)	0.2984 (4)	0.1424 (2)	0.0337 (7)
N22	0.3694 (4)	0.4602 (4)	0.1294 (2)	0.0350 (7)
H22A	0.4223	0.4823	0.1709	0.042*
N31	0.3204 (3)	0.1863 (4)	0.3744 (2)	0.0314 (7)
N32	0.1637 (3)	0.1746 (4)	0.3799 (2)	0.0331 (7)
H32A	0.1283	0.1307	0.3419	0.040*
C11	0.8379 (4)	−0.0898 (5)	0.2490 (3)	0.0347 (8)
C12	0.9861 (5)	−0.2312 (5)	0.2403 (3)	0.0443 (10)
H12	1.0932	−0.2237	0.2375	0.053*
C13	0.9699 (5)	−0.3839 (5)	0.2359 (3)	0.0512 (11)
H13	1.0683	−0.4808	0.2303	0.061*
C14	0.8112 (5)	−0.3972 (5)	0.2396 (3)	0.0437 (10)
H14	0.8016	−0.5008	0.2365	0.052*
C15	0.6684 (4)	−0.2511 (4)	0.2481 (2)	0.0328 (8)
C16	0.8196 (4)	0.0886 (5)	0.2600 (3)	0.0363 (8)
C17	0.4818 (5)	−0.2331 (5)	0.2587 (3)	0.0350 (8)
C21	0.2857 (5)	0.5808 (5)	0.0456 (3)	0.0375 (8)
C22	0.2196 (5)	0.4948 (5)	0.0004 (3)	0.0424 (9)
H22	0.1546	0.5431	−0.0597	0.051*
C23	0.2699 (5)	0.3211 (5)	0.0628 (3)	0.0377 (9)
C24	0.2736 (6)	0.7685 (5)	0.0153 (3)	0.0524 (11)
H24A	0.2520	0.8126	0.0731	0.079*
H24B	0.1810	0.8414	−0.0340	0.079*
H24C	0.3798	0.7723	−0.0126	0.079*
C25	0.2362 (6)	0.1690 (6)	0.0483 (3)	0.0555 (11)
H25A	0.1908	0.1150	0.1082	0.083*
H25B	0.3418	0.0819	0.0341	0.083*
H25C	0.1543	0.2128	−0.0069	0.083*
C31	0.0715 (4)	0.2404 (5)	0.4523 (3)	0.0344 (8)
C32	0.1727 (4)	0.2944 (5)	0.4958 (3)	0.0361 (8)
H32	0.1444	0.3447	0.5489	0.043*
C33	0.3257 (4)	0.2602 (4)	0.4457 (2)	0.0300 (8)
C34	−0.1051 (4)	0.2448 (6)	0.4742 (3)	0.0463 (10)
H34A	−0.1235	0.1620	0.4466	0.069*
H34B	−0.1884	0.3630	0.4445	0.069*
H34C	−0.1174	0.2121	0.5455	0.069*
C35	0.4794 (5)	0.2936 (6)	0.4643 (3)	0.0458 (10)
H35A	0.5760	0.1819	0.4864	0.069*
H35B	0.4554	0.3548	0.5150	0.069*
H35C	0.5057	0.3658	0.4033	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.0240 (2)	0.0284 (3)	0.0603 (3)	−0.01015 (18)	0.00311 (19)	−0.0211 (2)
O11	0.0298 (13)	0.0415 (15)	0.0719 (19)	−0.0164 (12)	0.0073 (13)	−0.0298 (14)
O12	0.0338 (15)	0.074 (2)	0.070 (2)	−0.0317 (14)	0.0095 (13)	−0.0341 (16)
O13	0.0317 (13)	0.0328 (14)	0.0679 (18)	−0.0128 (11)	−0.0016 (12)	−0.0216 (13)
O14	0.0624 (18)	0.0405 (16)	0.0659 (19)	−0.0304 (14)	0.0011 (14)	−0.0235 (14)
N11	0.0264 (14)	0.0292 (15)	0.0309 (15)	−0.0084 (12)	0.0004 (12)	−0.0099 (12)
N21	0.0346 (16)	0.0286 (16)	0.0452 (18)	−0.0157 (13)	0.0031 (14)	−0.0168 (13)
N22	0.0402 (17)	0.0316 (16)	0.0422 (18)	−0.0195 (14)	0.0032 (14)	−0.0159 (14)
N31	0.0228 (14)	0.0334 (16)	0.0435 (17)	−0.0137 (12)	0.0031 (12)	−0.0154 (13)
N32	0.0275 (15)	0.0378 (17)	0.0418 (18)	−0.0177 (13)	0.0037 (13)	−0.0163 (14)
C11	0.0294 (18)	0.041 (2)	0.0299 (19)	−0.0110 (16)	0.0026 (15)	−0.0092 (16)
C12	0.0291 (19)	0.052 (3)	0.044 (2)	−0.0086 (18)	0.0083 (17)	−0.0135 (19)
C13	0.046 (2)	0.040 (2)	0.049 (2)	0.0004 (19)	0.0159 (19)	−0.0142 (19)
C14	0.054 (2)	0.030 (2)	0.042 (2)	−0.0102 (18)	0.0095 (19)	−0.0140 (17)
C15	0.042 (2)	0.0288 (19)	0.0280 (18)	−0.0117 (16)	0.0020 (15)	−0.0115 (15)
C16	0.0307 (19)	0.045 (2)	0.038 (2)	−0.0175 (17)	−0.0014 (16)	−0.0151 (17)
C17	0.044 (2)	0.0299 (19)	0.033 (2)	−0.0163 (17)	−0.0036 (16)	−0.0080 (15)
C21	0.042 (2)	0.033 (2)	0.040 (2)	−0.0161 (17)	0.0095 (17)	−0.0135 (17)
C22	0.051 (2)	0.041 (2)	0.040 (2)	−0.0217 (19)	−0.0025 (18)	−0.0133 (18)
C23	0.042 (2)	0.034 (2)	0.042 (2)	−0.0176 (17)	0.0028 (17)	−0.0149 (17)
C24	0.072 (3)	0.034 (2)	0.054 (3)	−0.026 (2)	0.004 (2)	−0.0104 (19)
C25	0.072 (3)	0.047 (3)	0.063 (3)	−0.032 (2)	−0.010 (2)	−0.022 (2)
C31	0.0277 (18)	0.034 (2)	0.041 (2)	−0.0130 (16)	0.0045 (15)	−0.0096 (16)
C32	0.039 (2)	0.044 (2)	0.033 (2)	−0.0211 (18)	0.0062 (16)	−0.0168 (16)
C33	0.0290 (18)	0.0294 (18)	0.0334 (19)	−0.0135 (15)	−0.0015 (15)	−0.0077 (15)
C34	0.032 (2)	0.054 (3)	0.061 (3)	−0.0224 (19)	0.0146 (18)	−0.022 (2)
C35	0.038 (2)	0.060 (3)	0.053 (2)	−0.028 (2)	0.0018 (18)	−0.025 (2)

Geometric parameters (Å, º) top

Cu—N11	1.917 (3)	C14—C15	1.377 (5)
Cu—N21	2.172 (3)	C14—H14	0.9300
Cu—N31	1.994 (3)	C15—C17	1.523 (5)
Cu—O11	2.025 (2)	C21—C22	1.376 (5)
Cu—O13	2.006 (2)	C21—C24	1.491 (5)
O11—C16	1.274 (4)	C22—C23	1.390 (5)
O12—C16	1.225 (4)	C22—H22	0.9300
O13—C17	1.277 (4)	C23—C25	1.500 (5)
O14—C17	1.221 (4)	C24—H24A	0.9600
N11—C15	1.332 (4)	C24—H24B	0.9600
N11—C11	1.334 (4)	C24—H24C	0.9600
N21—C23	1.331 (4)	C25—H25A	0.9600
N21—N22	1.360 (4)	C25—H25B	0.9600
N22—C21	1.332 (5)	C25—H25C	0.9600
N22—H22A	0.8600	C31—C32	1.366 (5)
N31—C33	1.335 (4)	C31—C34	1.489 (5)
N31—N32	1.362 (3)	C32—C33	1.388 (5)
N32—C31	1.343 (4)	C32—H32	0.9300
N32—H32A	0.8600	C33—C35	1.492 (4)
C11—C12	1.380 (5)	C34—H34A	0.9600
C11—C16	1.516 (5)	C34—H34B	0.9600
C12—C13	1.378 (6)	C34—H34C	0.9600
C12—H12	0.9300	C35—H35A	0.9600
C13—C14	1.387 (6)	C35—H35B	0.9600
C13—H13	0.9300	C35—H35C	0.9600

N11—Cu—N31	149.17 (12)	O14—C17—O13	126.4 (4)
N11—Cu—O13	80.43 (11)	O14—C17—C15	119.8 (3)
N31—Cu—O13	92.70 (11)	O13—C17—C15	113.7 (3)
N11—Cu—O11	79.88 (11)	N22—C21—C22	106.1 (3)
N31—Cu—O11	102.35 (10)	N22—C21—C24	122.8 (3)
O13—Cu—O11	159.96 (10)	C22—C21—C24	131.1 (4)
N11—Cu—N21	113.60 (11)	C21—C22—C23	105.9 (3)
N31—Cu—N21	97.19 (11)	C21—C22—H22	127.0
O13—Cu—N21	101.01 (10)	C23—C22—H22	127.0
O11—Cu—N21	90.27 (11)	N21—C23—C22	110.8 (3)
C16—O11—Cu	115.7 (2)	N21—C23—C25	120.8 (3)
C17—O13—Cu	116.0 (2)	C22—C23—C25	128.4 (3)
C15—N11—C11	123.2 (3)	C21—C24—H24A	109.5
C15—N11—Cu	117.9 (2)	C21—C24—H24B	109.5
C11—N11—Cu	118.4 (2)	H24A—C24—H24B	109.5
C23—N21—N22	104.5 (3)	C21—C24—H24C	109.5
C23—N21—Cu	137.2 (2)	H24A—C24—H24C	109.5
N22—N21—Cu	118.3 (2)	H24B—C24—H24C	109.5
C21—N22—N21	112.7 (3)	C23—C25—H25A	109.5
C21—N22—H22A	123.6	C23—C25—H25B	109.5
N21—N22—H22A	123.6	H25A—C25—H25B	109.5
C33—N31—N32	105.7 (3)	C23—C25—H25C	109.5
C33—N31—Cu	135.3 (2)	H25A—C25—H25C	109.5
N32—N31—Cu	118.9 (2)	H25B—C25—H25C	109.5
C31—N32—N31	111.4 (3)	N32—C31—C32	106.3 (3)
C31—N32—H32A	124.3	N32—C31—C34	122.6 (3)
N31—N32—H32A	124.3	C32—C31—C34	131.1 (3)
N11—C11—C12	119.7 (3)	C31—C32—C33	107.0 (3)
N11—C11—C16	111.7 (3)	C31—C32—H32	126.5
C12—C11—C16	128.6 (3)	C33—C32—H32	126.5
C13—C12—C11	117.7 (4)	N31—C33—C32	109.5 (3)
C13—C12—H12	121.1	N31—C33—C35	121.9 (3)
C11—C12—H12	121.1	C32—C33—C35	128.5 (3)
C12—C13—C14	121.9 (3)	C31—C34—H34A	109.5
C12—C13—H13	119.0	C31—C34—H34B	109.5
C14—C13—H13	119.0	H34A—C34—H34B	109.5
C15—C14—C13	117.4 (4)	C31—C34—H34C	109.5
C15—C14—H14	121.3	H34A—C34—H34C	109.5
C13—C14—H14	121.3	H34B—C34—H34C	109.5
N11—C15—C14	120.0 (3)	C33—C35—H35A	109.5
N11—C15—C17	111.8 (3)	C33—C35—H35B	109.5
C14—C15—C17	128.2 (3)	H35A—C35—H35B	109.5
O12—C16—O11	126.2 (3)	C33—C35—H35C	109.5
O12—C16—C11	119.7 (3)	H35A—C35—H35C	109.5
O11—C16—C11	114.1 (3)	H35B—C35—H35C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N22—H22A···O14ⁱ	0.86	2.10	2.888 (4)	151
N32—H32A···O12ⁱⁱ	0.86	2.06	2.860 (4)	155

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

Experimental details

Crystal data
Chemical formula	[Cu(C₇H₃NO₄)(C₅H₈N₂)₂]
M_r	420.91
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.4572 (12), 8.5083 (12), 13.942 (2)
α, β, γ (°)	72.986 (2), 85.500 (2), 66.760 (2)
V (Å³)	880.7 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.28
Crystal size (mm)	0.23 × 0.15 × 0.13

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.775, 0.845
No. of measured, independent and observed [I > 2σ(I)] reflections	4570, 3036, 2497
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.106, 1.05
No. of reflections	3036
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.55

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Cu—N11	1.917 (3)	Cu—O11	2.025 (2)
Cu—N21	2.172 (3)	Cu—O13	2.006 (2)
Cu—N31	1.994 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N22—H22A···O14ⁱ	0.86	2.10	2.888 (4)	151
N32—H32A···O12ⁱⁱ	0.86	2.06	2.860 (4)	155

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

Acknowledgements

This project was supported by the Educational Development Foundation of Shanghai Educational Committee, China (grant No. AB0448).

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Haanstra, W. G., Van der Donk, W. A. J. W., Driessen, W. L., Reedijk, J., Wood, J. S. & Drew, M. G. B. (1990). J. Chem. Soc. Dalton Trans. pp. 3123–3128. CSD CrossRef Web of Science Google Scholar
Mukherjee, R. (2000). Coord. Chem. Rev. 203, 151–218. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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