(2-Oxido-1-naphthaldehyde benzoyl­hydrazonato-κ3N,N′,O)pyridine­copper(II)

Zou, L.-F.; Yang, X.-Y.; Gao, Y.; Yao, H.-B.; Li, Y.-H.

doi:10.1107/S1600536811011081

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page m511

doi:10.1107/S1600536811011081

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(2-Oxido-1-naphthaldehyde benzoylhydrazonato-κ³N,N′,O)pyridinecopper(II)

Li-Fei Zou,^a Xiu-Yun Yang,^a Ying Gao,^a Hai-Bo Yao ^a and Yun-Hui Li ^a ^*

^aSchool of Chemistry and Environmental Engineering, Changchun University of Science and Technology, Changchun, 130022, People's Republic of China
^*Correspondence e-mail: liyh@cust.edu.cn

(Received 18 March 2011; accepted 25 March 2011; online 31 March 2011)

In the mononuclear title compound, [Cu^II(C₁₈H₁₂N₂O₂)(C₅H₅N)], the Cu^II ion is coordinated by two O atoms and one N atom from the dianionic tridentate L²⁻ ligand (H₂L is 2-hydroxy-1-naphthaldehyde benzoylhydrazide) and one N atom from a pyridine molecule in a CuN₂O₂ distorted square-planar coordination environment.

Related literature

For the preparation of the Schiff base, see: Qiao et al. (2010 ). For chemically related applications arising from Schiff base compounds, see: Ando et al. (2004 ); Anford et al. (1998 ); Guo et al. (2010 ). For related structures, see: Ali et al. (2004 ); Sun et al. (2011 ); Xu et al. (2006 ); Yu et al. (2010 ).

Experimental

Crystal data

[Cu(C₁₈H₁₂N₂O₂)(C₅H₅N)]
M_r = 430.94
Monoclinic, P 2₁ /c
a = 11.6196 (6) Å
b = 8.4254 (4) Å
c = 19.6194 (10) Å
β = 106.247 (1)°
V = 1844.03 (16) Å³
Z = 4
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 185 K
0.14 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.849, T_max = 0.889
8559 measured reflections
3619 independent reflections
2860 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.086
S = 1.03
3619 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—O1	1.8853 (17)
Cu1—N1	1.902 (2)
Cu1—O2	1.9243 (17)
Cu1—N3	2.001 (2)

O1—Cu1—N1	93.17 (8)
O1—Cu1—O2	172.59 (7)
N1—Cu1—O2	81.30 (8)
O1—Cu1—N3	93.65 (8)
N1—Cu1—N3	171.07 (8)
O2—Cu1—N3	92.37 (8)

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011081/zq2095sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011081/zq2095Isup2.hkl

checkCIF report

Comment top

Interest in the chemistry of Schiff base arises from their ability to bind to metal ions (Yu et al., 2010) as well as their antitumor activities and magnetochemistry (Ando et al., 2004; Guo et al., 2010). In fact, with some acylhydrazone ligands, their metal compounds are endowed with significantly improved industrial processes (Anford et al., 1998). We selected the 2-hydroxy-1-naphthaldehyde benzoylhydrazide (H₂L) Schiff base ligand to construct coordination polymers with defined geometry, due to its combination of nitrogen and oxygen donor atoms. We report here the preparation and crystal structure of the Schiff base Cu^II title compound.

The present compound, [Cu^II(C₁₈H₁₂N₂O₂)(C₅H₅N)], together with the atom-numbering scheme, is illustrated in Fig. 1. Selected bond lengths and angles are given in Table 1. The Cu^II ion is coordinated by two O atoms and one N atom from the dianionic tridentate ligand L^2- ligand (H₂L is 2-hydroxy-1-naphthaldehyde benzoylhydrazide), and one N atom from a pyridine molecule. The Cu^II ion adopts a CuN₂O₂ distorted square-planar coordination environment. The Cu—O and Cu—N bond distances are similar to the corresponding bond distances observed in related compounds (Ali et al., 2004; Xu et al., 2006; Sun et al., 2011). There is no significant deviation of the metal centre from the N₂O₂ equatorial plane. The maximum displacements from the least-squares plane through N1, N3, O1, and O2 (rms deviation = 0.0895 Å) are 0.096 (1) and -0.094 (1) Å for atoms N1 and O2; Cu1 is -0.013 (1) Å below the mean plane. The coordinated pyridine molecule is almost coplanar with the previous N₂O₂ plane, the dihedral angle between the mean planes is 7.2 (1)°.

Related literature top

For the preparation of the Schiff base, see: Qiao et al. (2010). For chemically related applications arising from Schiff base compounds, see: Ando et al. (2004); Anford et al. (1998); Guo et al. (2010). For related structures, see: Ali et al. (2004); Sun et al. (2011); Xu et al. (2006); Yu et al. (2010).

Experimental top

The 2-hydroxy-1-naphthaldehyde benzoylhydrazide ligand (H₂L) was prepared in a similar manner to the reported procedures (Qiao et al., 2010). The title compound was synthesized by adding pyridine (0.2 mL) to a solution of H₂L (0.1 mmol) and Cu(OAc)₂ (0.1 mmol) in methanol/dichloromethane (1:1, 20 mL), and the resulting mixture was stirred for about 6 h to afford a green solution. A week later, brown crystals of the title compound were isolated from the solution.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. A view of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.

(2-Oxido-1-naphthaldehyde benzoylhydrazonato-κ³N,N', O)pyridinecopper(II) top

Crystal data top

[Cu(C₁₈H₁₂N₂O₂)(C₅H₅N)]	F(000) = 884
M_r = 430.94	D_x = 1.552 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9033 reflections
a = 11.6196 (6) Å	θ = 4.8–51.9°
b = 8.4254 (4) Å	µ = 1.21 mm⁻¹
c = 19.6194 (10) Å	T = 185 K
β = 106.247 (1)°	Block, brown
V = 1844.03 (16) Å³	0.14 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD area detector diffractometer	3619 independent reflections
Radiation source: fine-focus sealed tube	2860 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
phi and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
T_min = 0.849, T_max = 0.889	k = −6→10
8559 measured reflections	l = −18→24

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0353P)² + 1.0945P] where P = (F_o² + 2F_c²)/3
3619 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Cu(C₁₈H₁₂N₂O₂)(C₅H₅N)]	V = 1844.03 (16) Å³
M_r = 430.94	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6196 (6) Å	µ = 1.21 mm⁻¹
b = 8.4254 (4) Å	T = 185 K
c = 19.6194 (10) Å	0.14 × 0.12 × 0.10 mm
β = 106.247 (1)°

Data collection top

Bruker APEXII CCD area detector diffractometer	3619 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2860 reflections with I > 2σ(I)
T_min = 0.849, T_max = 0.889	R_int = 0.031
8559 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.03	Δρ_max = 0.46 e Å⁻³
3619 reflections	Δρ_min = −0.29 e Å⁻³
262 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	0.86976 (3)	0.13588 (4)	0.539632 (16)	0.02191 (11)
N1	0.89789 (18)	0.1188 (2)	0.44895 (11)	0.0200 (5)
N2	0.99966 (18)	0.1976 (3)	0.44156 (11)	0.0216 (5)
N3	0.86766 (19)	0.1483 (2)	0.64115 (11)	0.0226 (5)
O1	0.72604 (15)	0.0186 (2)	0.51138 (9)	0.0247 (4)
O2	1.00963 (15)	0.2688 (2)	0.55668 (9)	0.0238 (4)
C1	0.7084 (2)	−0.1291 (3)	0.26471 (14)	0.0265 (6)
H1	0.7807	−0.0755	0.2655	0.032*
C2	0.6465 (3)	−0.2069 (3)	0.20399 (14)	0.0300 (6)
H2	0.6762	−0.2046	0.1635	0.036*
C3	0.5411 (3)	−0.2891 (3)	0.20059 (15)	0.0306 (6)
H3	0.4997	−0.3440	0.1586	0.037*
C4	0.4982 (3)	−0.2894 (3)	0.25876 (15)	0.0313 (7)
H4	0.4259	−0.3444	0.2567	0.038*
C5	0.5588 (2)	−0.2100 (3)	0.32154 (14)	0.0261 (6)
C6	0.5135 (2)	−0.2110 (3)	0.38178 (15)	0.0295 (6)
H6	0.4416	−0.2672	0.3794	0.035*
C7	0.5702 (2)	−0.1339 (3)	0.44258 (14)	0.0267 (6)
H7	0.5366	−0.1366	0.4815	0.032*
C8	0.6791 (2)	−0.0489 (3)	0.44957 (13)	0.0221 (6)
C9	0.7276 (2)	−0.0447 (3)	0.39116 (13)	0.0205 (5)
C10	0.6671 (2)	−0.1266 (3)	0.32608 (13)	0.0225 (6)
C11	0.8363 (2)	0.0379 (3)	0.39455 (13)	0.0216 (6)
H11	0.8658	0.0333	0.3541	0.026*
C12	1.0481 (2)	0.2750 (3)	0.50057 (13)	0.0213 (6)
C13	1.1522 (2)	0.3790 (3)	0.50397 (14)	0.0219 (6)
C14	1.1922 (3)	0.4090 (3)	0.44463 (15)	0.0329 (7)
H14	1.1537	0.3597	0.4006	0.039*
C15	1.2877 (3)	0.5103 (4)	0.44947 (16)	0.0385 (7)
H15	1.3142	0.5301	0.4086	0.046*
C16	1.3449 (3)	0.5828 (3)	0.51292 (17)	0.0361 (7)
H16	1.4105	0.6522	0.5158	0.043*
C17	1.3063 (2)	0.5537 (3)	0.57197 (16)	0.0328 (7)
H17	1.3455	0.6032	0.6158	0.039*
C18	1.2107 (2)	0.4527 (3)	0.56769 (14)	0.0262 (6)
H18	1.1847	0.4334	0.6087	0.031*
C19	0.9510 (2)	0.2352 (3)	0.68806 (15)	0.0323 (7)
H19	1.0071	0.2946	0.6714	0.039*
C20	0.9577 (3)	0.2408 (4)	0.75936 (15)	0.0350 (7)
H20	1.0176	0.3027	0.7911	0.042*
C21	0.8762 (3)	0.1554 (3)	0.78380 (14)	0.0313 (7)
H21	0.8795	0.1564	0.8327	0.038*
C22	0.7900 (3)	0.0686 (4)	0.73614 (15)	0.0332 (7)
H22	0.7319	0.0101	0.7515	0.040*
C23	0.7889 (2)	0.0676 (3)	0.66537 (14)	0.0275 (6)
H23	0.7294	0.0067	0.6328	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02087 (18)	0.02664 (19)	0.01893 (17)	−0.00342 (14)	0.00672 (13)	−0.00051 (14)
N1	0.0180 (11)	0.0199 (11)	0.0215 (11)	−0.0023 (9)	0.0045 (9)	0.0025 (9)
N2	0.0180 (11)	0.0242 (11)	0.0227 (11)	−0.0027 (9)	0.0062 (9)	0.0032 (9)
N3	0.0222 (11)	0.0258 (12)	0.0204 (11)	−0.0017 (10)	0.0069 (9)	−0.0012 (9)
O1	0.0248 (10)	0.0274 (10)	0.0233 (10)	−0.0047 (8)	0.0092 (8)	−0.0023 (8)
O2	0.0240 (10)	0.0289 (10)	0.0201 (9)	−0.0047 (8)	0.0085 (8)	−0.0025 (8)
C1	0.0250 (14)	0.0242 (14)	0.0281 (14)	0.0001 (12)	0.0037 (12)	0.0004 (12)
C2	0.0352 (16)	0.0268 (15)	0.0262 (15)	0.0026 (13)	0.0053 (13)	−0.0006 (12)
C3	0.0333 (16)	0.0248 (15)	0.0277 (15)	0.0017 (13)	−0.0016 (13)	−0.0075 (12)
C4	0.0269 (15)	0.0256 (15)	0.0353 (16)	−0.0040 (12)	−0.0011 (13)	−0.0040 (13)
C5	0.0266 (15)	0.0196 (14)	0.0296 (15)	−0.0009 (11)	0.0038 (12)	0.0018 (12)
C6	0.0249 (15)	0.0262 (15)	0.0367 (17)	−0.0071 (12)	0.0073 (13)	0.0012 (13)
C7	0.0243 (14)	0.0267 (15)	0.0298 (15)	−0.0027 (12)	0.0086 (12)	0.0036 (12)
C8	0.0223 (13)	0.0189 (13)	0.0235 (14)	0.0012 (11)	0.0039 (11)	0.0027 (11)
C9	0.0202 (13)	0.0175 (13)	0.0217 (13)	0.0002 (10)	0.0025 (11)	0.0018 (10)
C10	0.0219 (13)	0.0178 (13)	0.0249 (14)	0.0031 (11)	0.0018 (11)	0.0029 (11)
C11	0.0248 (14)	0.0208 (13)	0.0201 (13)	0.0033 (11)	0.0076 (11)	0.0037 (11)
C12	0.0221 (14)	0.0214 (14)	0.0208 (13)	0.0040 (11)	0.0067 (11)	0.0038 (11)
C13	0.0199 (13)	0.0195 (13)	0.0261 (14)	0.0014 (11)	0.0061 (11)	0.0034 (11)
C14	0.0372 (17)	0.0342 (16)	0.0293 (16)	−0.0103 (13)	0.0127 (13)	−0.0024 (13)
C15	0.0434 (19)	0.0386 (18)	0.0400 (18)	−0.0107 (15)	0.0222 (15)	0.0020 (14)
C16	0.0311 (16)	0.0264 (15)	0.054 (2)	−0.0115 (13)	0.0172 (15)	−0.0010 (14)
C17	0.0294 (16)	0.0286 (16)	0.0384 (17)	−0.0077 (13)	0.0063 (13)	−0.0087 (13)
C18	0.0271 (15)	0.0243 (14)	0.0284 (15)	−0.0013 (12)	0.0096 (12)	−0.0040 (12)
C19	0.0306 (16)	0.0393 (17)	0.0291 (15)	−0.0132 (14)	0.0119 (13)	−0.0048 (13)
C20	0.0385 (17)	0.0398 (18)	0.0264 (15)	−0.0112 (14)	0.0087 (13)	−0.0066 (13)
C21	0.0429 (17)	0.0316 (16)	0.0214 (14)	−0.0048 (13)	0.0120 (13)	−0.0026 (12)
C22	0.0374 (17)	0.0374 (17)	0.0287 (15)	−0.0117 (14)	0.0156 (13)	−0.0043 (13)
C23	0.0268 (15)	0.0327 (15)	0.0235 (14)	−0.0072 (12)	0.0075 (12)	−0.0031 (12)

Geometric parameters (Å, º) top

Cu1—O1	1.8853 (17)	C8—C9	1.412 (3)
Cu1—N1	1.902 (2)	C9—C11	1.428 (3)
Cu1—O2	1.9243 (17)	C9—C10	1.449 (3)
Cu1—N3	2.001 (2)	C11—H11	0.9500
N1—C11	1.300 (3)	C12—C13	1.480 (3)
N1—N2	1.398 (3)	C13—C18	1.391 (4)
N2—C12	1.311 (3)	C13—C14	1.392 (4)
N3—C23	1.331 (3)	C14—C15	1.381 (4)
N3—C19	1.349 (3)	C14—H14	0.9500
O1—C8	1.312 (3)	C15—C16	1.379 (4)
O2—C12	1.300 (3)	C15—H15	0.9500
C1—C2	1.374 (4)	C16—C17	1.376 (4)
C1—C10	1.415 (4)	C16—H16	0.9500
C1—H1	0.9500	C17—C18	1.384 (4)
C2—C3	1.392 (4)	C17—H17	0.9500
C2—H2	0.9500	C18—H18	0.9500
C3—C4	1.367 (4)	C19—C20	1.380 (4)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.405 (4)	C20—C21	1.378 (4)
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.422 (4)	C21—C22	1.374 (4)
C5—C10	1.423 (4)	C21—H21	0.9500
C6—C7	1.356 (4)	C22—C23	1.385 (4)
C6—H6	0.9500	C22—H22	0.9500
C7—C8	1.427 (4)	C23—H23	0.9500
C7—H7	0.9500

O1—Cu1—N1	93.17 (8)	C1—C10—C5	116.4 (2)
O1—Cu1—O2	172.59 (7)	C1—C10—C9	124.1 (2)
N1—Cu1—O2	81.30 (8)	C5—C10—C9	119.6 (2)
O1—Cu1—N3	93.65 (8)	N1—C11—C9	124.8 (2)
N1—Cu1—N3	171.07 (8)	N1—C11—H11	117.6
O2—Cu1—N3	92.37 (8)	C9—C11—H11	117.6
C11—N1—N2	116.8 (2)	O2—C12—N2	124.3 (2)
C11—N1—Cu1	127.48 (17)	O2—C12—C13	117.2 (2)
N2—N1—Cu1	115.64 (15)	N2—C12—C13	118.6 (2)
C12—N2—N1	108.15 (19)	C18—C13—C14	118.5 (2)
C23—N3—C19	117.9 (2)	C18—C13—C12	119.5 (2)
C23—N3—Cu1	121.99 (18)	C14—C13—C12	122.0 (2)
C19—N3—Cu1	120.08 (17)	C15—C14—C13	120.3 (3)
C8—O1—Cu1	127.16 (16)	C15—C14—H14	119.9
C12—O2—Cu1	110.51 (16)	C13—C14—H14	119.9
C2—C1—C10	121.7 (3)	C16—C15—C14	120.7 (3)
C2—C1—H1	119.2	C16—C15—H15	119.6
C10—C1—H1	119.2	C14—C15—H15	119.6
C1—C2—C3	121.3 (3)	C17—C16—C15	119.5 (3)
C1—C2—H2	119.4	C17—C16—H16	120.2
C3—C2—H2	119.4	C15—C16—H16	120.2
C4—C3—C2	118.8 (3)	C16—C17—C18	120.2 (3)
C4—C3—H3	120.6	C16—C17—H17	119.9
C2—C3—H3	120.6	C18—C17—H17	119.9
C3—C4—C5	121.4 (3)	C17—C18—C13	120.7 (3)
C3—C4—H4	119.3	C17—C18—H18	119.6
C5—C4—H4	119.3	C13—C18—H18	119.6
C4—C5—C6	121.0 (3)	N3—C19—C20	122.5 (3)
C4—C5—C10	120.5 (3)	N3—C19—H19	118.8
C6—C5—C10	118.5 (2)	C20—C19—H19	118.8
C7—C6—C5	121.8 (2)	C21—C20—C19	119.0 (3)
C7—C6—H6	119.1	C21—C20—H20	120.5
C5—C6—H6	119.1	C19—C20—H20	120.5
C6—C7—C8	121.7 (2)	C22—C21—C20	118.8 (3)
C6—C7—H7	119.2	C22—C21—H21	120.6
C8—C7—H7	119.2	C20—C21—H21	120.6
O1—C8—C9	125.6 (2)	C21—C22—C23	119.1 (3)
O1—C8—C7	115.8 (2)	C21—C22—H22	120.4
C9—C8—C7	118.6 (2)	C23—C22—H22	120.4
C8—C9—C11	121.6 (2)	N3—C23—C22	122.7 (3)
C8—C9—C10	119.9 (2)	N3—C23—H23	118.6
C11—C9—C10	118.6 (2)	C22—C23—H23	118.6

Experimental details

Crystal data
Chemical formula	[Cu(C₁₈H₁₂N₂O₂)(C₅H₅N)]
M_r	430.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	185
a, b, c (Å)	11.6196 (6), 8.4254 (4), 19.6194 (10)
β (°)	106.247 (1)
V (Å³)	1844.03 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.14 × 0.12 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.849, 0.889
No. of measured, independent and observed [I > 2σ(I)] reflections	8559, 3619, 2860
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.086, 1.03
No. of reflections	3619
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.29

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Cu1—O1	1.8853 (17)	Cu1—O2	1.9243 (17)
Cu1—N1	1.902 (2)	Cu1—N3	2.001 (2)

O1—Cu1—N1	93.17 (8)	O1—Cu1—N3	93.65 (8)
O1—Cu1—O2	172.59 (7)	N1—Cu1—N3	171.07 (8)
N1—Cu1—O2	81.30 (8)	O2—Cu1—N3	92.37 (8)

Acknowledgements

We thank the project supported by Jilin Provincial Science & Technology Department (20090535) and Changchun University of Science and Technology for financial support.

References

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