(Dimethyl­formamide-κO)[2-meth­oxy-6-(2-pyridylmethyl­imino­meth­yl)phenolato-κ3N,N′,O1](thio­cyanato-κN)copper(II)

Bao, Q.; Chen, X.; Rong, R.; Shi, F.

doi:10.1107/S1600536810014212

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page m563

https://doi.org/10.1107/S1600536810014212

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(Dimethylformamide-κO)[2-methoxy-6-(2-pyridylmethyliminomethyl)phenolato-κ³N,N′,O¹](thiocyanato-κN)copper(II)

Qianqian Bao,^a Xiaodan Chen,^a ^* Rong Rong ^b and Feifei Shi ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China, and ^bDepartment of Chemistry, Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan University, Kunming 650091, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 16 April 2010; accepted 18 April 2010; online 24 April 2010)

In the title compound, [Cu(C₁₄H₁₃N₂O₂)(NCS)(C₃H₇NO)], the Cu²⁺ ion is coordinated by an N,N′,O-tridentate 2-methoxy-6-(2-pyridylmethyliminomethyl)phenolate ligand, an N-bonded thiocyanate ion and an O-bonded dimethylformamide (DMF) molecule, resulting in a distorted CuN₃O₂ square-based pyramidal geometry for the metal ion, with the DMF O atom in the apical site. The dihedral angle between the aromatic rings in the ligand is 8.70 (16)°. The S atom is disordered over two positions in a 0.901 (6):0.099 (6) ratio. In the crystal, molecules interact by way of π–π stacking interactions [centroid–centroid separation = 3.720 (2) Å].

Related literature

For the synthesis, see: Pointeau et al. (1986 ). For related structures, see: Li & Zhang (2004 ); You & Zhu (2004 ).

Experimental

Crystal data

[Cu(C₁₄H₁₃N₂O₂)(NCS)(C₃H₇NO)]
M_r = 435.98
Triclinic, $[P \overline 1]$
a = 8.6768 (9) Å
b = 10.9310 (11) Å
c = 11.0689 (12) Å
α = 83.251 (2)°
β = 72.023 (1)°
γ = 79.530 (1)°
V = 979.84 (18) Å³
Z = 2
Mo Kα radiation
μ = 1.25 mm⁻¹
T = 298 K
0.20 × 0.12 × 0.09 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.737, T_max = 0.868
5129 measured reflections
3392 independent reflections
2679 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.090
S = 1.09
3392 reflections
251 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—O1	1.905 (2)
Cu1—N1	1.942 (2)
Cu1—N3	1.971 (3)
Cu1—N2	2.012 (2)
Cu1—O3	2.392 (2)

O1—Cu1—N1	92.88 (9)
O1—Cu1—N3	90.19 (9)
N1—Cu1—N3	168.56 (9)
O1—Cu1—N2	173.84 (9)
N1—Cu1—N2	82.13 (10)
N3—Cu1—N2	94.01 (10)
O1—Cu1—O3	93.96 (8)
N1—Cu1—O3	96.07 (8)
N3—Cu1—O3	94.71 (9)
N2—Cu1—O3	90.18 (8)

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810014212/hb5406sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014212/hb5406Isup2.hkl

checkCIF report

Related literature top

For the synthesis, see: Pointeau et al. (1986). For related structures, see: Li & Zhang (2004); You & Zhu (2004).

Experimental top

3-Methoxysalicylaldehyde (0.0152 g, 0.1 mmol) dissolved in methanol (5 ml) was added to a methanol solution (5 ml) of 2-aminopyridine (0.0108 g, 0.1 mmol) with slowly stirring. The resulting yellow solution was continuously stirred for about 1 h, then CuCl₂.2H₂O (0.017 g, 0.1 mmol) in 5 ml water and potassium thiocyanate (0.019 g, 0.2 mmol) in 2 ml methanol were added with stirring. The precipitate was collected by filtration, dissolved with N,N-dimethyllformamide. Brown prisms of (I) were obtained by slow evaporation at room temperature over several days.

Structure description top

For the synthesis, see: Pointeau et al. (1986). For related structures, see: Li & Zhang (2004); You & Zhu (2004).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.

(Dimethylformamide-κO)[2-methoxy-6-(2- pyridylmethyliminomethyl)phenolato- κ³N,N,O¹](thiocyanato-κN)copper(II) top

Crystal data top

[Cu(C₁₄H₁₃N₂O₂)(NCS)(C₃H₇NO)]	Z = 2
M_r = 435.98	F(000) = 450
Triclinic, P1	D_x = 1.478 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6768 (9) Å	Cell parameters from 13380 reflections
b = 10.9310 (11) Å	θ = 3.0–27.6°
c = 11.0689 (12) Å	µ = 1.25 mm⁻¹
α = 83.251 (2)°	T = 298 K
β = 72.023 (1)°	Prism, dark brown
γ = 79.530 (1)°	0.20 × 0.12 × 0.09 mm
V = 979.84 (18) Å³

Data collection top

Rigaku SCXmini diffractometer	3392 independent reflections
Radiation source: fine-focus sealed tube	2679 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 8.192 pixels mm^-1	θ_max = 25.0°, θ_min = 1.9°
Thin–slice ω scans	h = −9→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→7
T_min = 0.737, T_max = 0.868	l = −12→13
5129 measured reflections

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) = 0.090	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.039P)² + 0.2715P] where P = (F_o² + 2F_c²)/3
3392 reflections	(Δ/σ)_max = 0.001
251 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Cu(C₁₄H₁₃N₂O₂)(NCS)(C₃H₇NO)]	γ = 79.530 (1)°
M_r = 435.98	V = 979.84 (18) Å³
Triclinic, P1	Z = 2
a = 8.6768 (9) Å	Mo Kα radiation
b = 10.9310 (11) Å	µ = 1.25 mm⁻¹
c = 11.0689 (12) Å	T = 298 K
α = 83.251 (2)°	0.20 × 0.12 × 0.09 mm
β = 72.023 (1)°

Data collection top

Rigaku SCXmini diffractometer	3392 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2679 reflections with I > 2σ(I)
T_min = 0.737, T_max = 0.868	R_int = 0.016
5129 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.09	Δρ_max = 0.33 e Å⁻³
3392 reflections	Δρ_min = −0.37 e Å⁻³
251 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 > 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	Occ. (<1)
Cu1	0.63382 (4)	0.88140 (3)	0.58156 (3)	0.03823 (14)
S1	0.1914 (3)	0.73555 (19)	0.89276 (15)	0.0641 (6)	0.901 (6)
S1'	0.255 (2)	0.6960 (16)	0.9198 (14)	0.0641 (6)	0.099 (6)
N1	0.7507 (3)	0.9830 (2)	0.4385 (2)	0.0367 (5)
N2	0.6888 (3)	1.0010 (2)	0.6814 (2)	0.0386 (6)
N3	0.4812 (3)	0.8079 (2)	0.7321 (2)	0.0450 (6)
N4	0.9692 (3)	0.5684 (2)	0.7084 (3)	0.0512 (7)
O1	0.5788 (2)	0.78300 (18)	0.47433 (19)	0.0442 (5)
O2	0.4899 (3)	0.61550 (19)	0.3729 (2)	0.0514 (6)
O3	0.8691 (3)	0.73557 (19)	0.5981 (2)	0.0545 (6)
C1	0.7883 (3)	0.9606 (3)	0.3205 (3)	0.0405 (7)
H1	0.8535	1.0123	0.2618	0.049*
C2	0.7394 (3)	0.8639 (3)	0.2710 (3)	0.0385 (7)
C3	0.6353 (3)	0.7818 (3)	0.3508 (3)	0.0385 (7)
C4	0.5880 (4)	0.6919 (3)	0.2902 (3)	0.0430 (7)
C5	0.6418 (4)	0.6871 (3)	0.1600 (3)	0.0514 (8)
H5	0.6084	0.6291	0.1223	0.062*
C6	0.7457 (4)	0.7678 (3)	0.0834 (3)	0.0575 (9)
H6	0.7818	0.7628	−0.0044	0.069*
C7	0.7939 (4)	0.8537 (3)	0.1377 (3)	0.0507 (8)
H7	0.8639	0.9066	0.0863	0.061*
C8	0.4532 (5)	0.5136 (3)	0.3227 (4)	0.0697 (11)
H8A	0.3792	0.5445	0.2732	0.105*
H8B	0.4032	0.4579	0.3914	0.105*
H8C	0.5526	0.4698	0.2696	0.105*
C9	0.8024 (4)	1.0923 (3)	0.4699 (3)	0.0417 (7)
H9A	0.7397	1.1677	0.4433	0.050*
H9B	0.9175	1.0936	0.4252	0.050*
C10	0.7757 (3)	1.0878 (3)	0.6111 (3)	0.0388 (7)
C11	0.8352 (4)	1.1694 (3)	0.6660 (3)	0.0479 (8)
H11	0.8973	1.2277	0.6155	0.058*
C12	0.8012 (4)	1.1628 (3)	0.7959 (3)	0.0525 (8)
H12	0.8393	1.2173	0.8345	0.063*
C13	0.7099 (4)	1.0746 (3)	0.8691 (3)	0.0550 (9)
H13	0.6850	1.0692	0.9573	0.066*
C14	0.6569 (4)	0.9956 (3)	0.8089 (3)	0.0496 (8)
H14	0.5964	0.9356	0.8579	0.059*
C15	0.3643 (4)	0.7751 (3)	0.7999 (3)	0.0399 (7)
C16	0.8581 (4)	0.6634 (3)	0.6928 (3)	0.0490 (8)
H16	0.7623	0.6769	0.7599	0.059*
C17	0.9490 (5)	0.4915 (4)	0.8262 (4)	0.0790 (12)
H17A	1.0281	0.5039	0.8662	0.118*
H17B	0.9649	0.4055	0.8087	0.118*
H17C	0.8405	0.5142	0.8820	0.118*
C18	1.1236 (5)	0.5440 (4)	0.6098 (4)	0.0901 (14)
H18A	1.1135	0.5866	0.5310	0.135*
H18B	1.1522	0.4559	0.5996	0.135*
H18C	1.2077	0.5731	0.6333	0.135*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0348 (2)	0.0348 (2)	0.0399 (2)	−0.00972 (15)	−0.00338 (15)	0.00433 (15)
S1	0.0534 (10)	0.0732 (10)	0.0568 (7)	−0.0317 (8)	0.0074 (7)	0.0010 (6)
S1'	0.0534 (10)	0.0732 (10)	0.0568 (7)	−0.0317 (8)	0.0074 (7)	0.0010 (6)
N1	0.0332 (13)	0.0317 (13)	0.0418 (15)	−0.0070 (10)	−0.0076 (11)	0.0055 (10)
N2	0.0333 (13)	0.0359 (14)	0.0412 (15)	−0.0073 (10)	−0.0041 (11)	0.0034 (11)
N3	0.0414 (14)	0.0411 (15)	0.0473 (16)	−0.0123 (12)	−0.0039 (13)	0.0023 (12)
N4	0.0492 (16)	0.0414 (16)	0.0636 (18)	−0.0062 (13)	−0.0228 (14)	0.0096 (13)
O1	0.0451 (12)	0.0429 (12)	0.0410 (13)	−0.0173 (9)	−0.0029 (10)	0.0004 (9)
O2	0.0515 (13)	0.0434 (13)	0.0574 (14)	−0.0159 (10)	−0.0072 (11)	−0.0065 (10)
O3	0.0445 (13)	0.0485 (14)	0.0601 (15)	0.0008 (10)	−0.0118 (11)	0.0156 (11)
C1	0.0311 (15)	0.0377 (17)	0.0450 (19)	−0.0043 (13)	−0.0058 (13)	0.0120 (13)
C2	0.0321 (15)	0.0351 (16)	0.0425 (18)	−0.0011 (12)	−0.0070 (13)	0.0034 (13)
C3	0.0310 (15)	0.0325 (16)	0.0461 (19)	0.0040 (12)	−0.0092 (13)	0.0006 (13)
C4	0.0359 (16)	0.0380 (17)	0.052 (2)	−0.0006 (13)	−0.0120 (14)	−0.0023 (14)
C5	0.052 (2)	0.050 (2)	0.054 (2)	−0.0060 (16)	−0.0167 (17)	−0.0080 (16)
C6	0.065 (2)	0.063 (2)	0.0405 (19)	−0.0064 (18)	−0.0121 (17)	−0.0028 (16)
C7	0.0478 (19)	0.054 (2)	0.0447 (19)	−0.0083 (15)	−0.0085 (15)	0.0073 (15)
C8	0.071 (2)	0.055 (2)	0.084 (3)	−0.0228 (19)	−0.012 (2)	−0.021 (2)
C9	0.0393 (16)	0.0373 (17)	0.0471 (19)	−0.0141 (13)	−0.0109 (14)	0.0100 (13)
C10	0.0282 (14)	0.0326 (16)	0.0502 (19)	−0.0010 (12)	−0.0074 (13)	0.0014 (13)
C11	0.0413 (17)	0.0449 (19)	0.056 (2)	−0.0119 (14)	−0.0129 (15)	0.0064 (15)
C12	0.052 (2)	0.050 (2)	0.060 (2)	−0.0109 (16)	−0.0202 (17)	−0.0063 (16)
C13	0.059 (2)	0.058 (2)	0.046 (2)	−0.0076 (17)	−0.0131 (17)	−0.0038 (16)
C14	0.0510 (19)	0.0473 (19)	0.047 (2)	−0.0154 (15)	−0.0074 (16)	0.0042 (15)
C15	0.0478 (18)	0.0331 (16)	0.0367 (17)	−0.0109 (14)	−0.0066 (15)	−0.0022 (13)
C16	0.0421 (18)	0.0425 (19)	0.059 (2)	−0.0060 (15)	−0.0104 (16)	−0.0016 (16)
C17	0.090 (3)	0.068 (3)	0.080 (3)	−0.016 (2)	−0.039 (2)	0.032 (2)
C18	0.061 (2)	0.090 (3)	0.092 (3)	0.024 (2)	−0.012 (2)	0.016 (2)

Geometric parameters (Å, º) top

Cu1—O1	1.905 (2)	C5—H5	0.9300
Cu1—N1	1.942 (2)	C6—C7	1.358 (5)
Cu1—N3	1.971 (3)	C6—H6	0.9300
Cu1—N2	2.012 (2)	C7—H7	0.9300
Cu1—O3	2.392 (2)	C8—H8A	0.9600
S1—C15	1.635 (3)	C8—H8B	0.9600
S1'—C15	1.633 (13)	C8—H8C	0.9600
N1—C1	1.287 (4)	C9—C10	1.504 (4)
N1—C9	1.463 (3)	C9—H9A	0.9700
N2—C10	1.342 (4)	C9—H9B	0.9700
N2—C14	1.347 (4)	C10—C11	1.385 (4)
N3—C15	1.149 (4)	C11—C12	1.372 (4)
N4—C16	1.317 (4)	C11—H11	0.9300
N4—C18	1.447 (5)	C12—C13	1.383 (4)
N4—C17	1.447 (4)	C12—H12	0.9300
O1—C3	1.304 (3)	C13—C14	1.368 (4)
O2—C4	1.364 (4)	C13—H13	0.9300
O2—C8	1.426 (4)	C14—H14	0.9300
O3—C16	1.225 (4)	C16—H16	0.9300
C1—C2	1.427 (4)	C17—H17A	0.9600
C1—H1	0.9300	C17—H17B	0.9600
C2—C7	1.416 (4)	C17—H17C	0.9600
C2—C3	1.420 (4)	C18—H18A	0.9600
C3—C4	1.433 (4)	C18—H18B	0.9600
C4—C5	1.375 (4)	C18—H18C	0.9600
C5—C6	1.397 (5)

O1—Cu1—N1	92.88 (9)	O2—C8—H8B	109.5
O1—Cu1—N3	90.19 (9)	H8A—C8—H8B	109.5
N1—Cu1—N3	168.56 (9)	O2—C8—H8C	109.5
O1—Cu1—N2	173.84 (9)	H8A—C8—H8C	109.5
N1—Cu1—N2	82.13 (10)	H8B—C8—H8C	109.5
N3—Cu1—N2	94.01 (10)	N1—C9—C10	109.5 (2)
O1—Cu1—O3	93.96 (8)	N1—C9—H9A	109.8
N1—Cu1—O3	96.07 (8)	C10—C9—H9A	109.8
N3—Cu1—O3	94.71 (9)	N1—C9—H9B	109.8
N2—Cu1—O3	90.18 (8)	C10—C9—H9B	109.8
C1—N1—C9	118.2 (2)	H9A—C9—H9B	108.2
C1—N1—Cu1	125.6 (2)	N2—C10—C11	121.8 (3)
C9—N1—Cu1	116.20 (18)	N2—C10—C9	116.1 (3)
C10—N2—C14	118.4 (3)	C11—C10—C9	122.2 (3)
C10—N2—Cu1	115.2 (2)	C12—C11—C10	119.0 (3)
C14—N2—Cu1	126.2 (2)	C12—C11—H11	120.5
C15—N3—Cu1	161.4 (3)	C10—C11—H11	120.5
C16—N4—C18	120.1 (3)	C11—C12—C13	119.5 (3)
C16—N4—C17	122.3 (3)	C11—C12—H12	120.2
C18—N4—C17	117.5 (3)	C13—C12—H12	120.2
C3—O1—Cu1	127.30 (19)	C14—C13—C12	118.5 (3)
C4—O2—C8	117.7 (3)	C14—C13—H13	120.7
C16—O3—Cu1	119.2 (2)	C12—C13—H13	120.7
N1—C1—C2	126.2 (3)	N2—C14—C13	122.7 (3)
N1—C1—H1	116.9	N2—C14—H14	118.6
C2—C1—H1	116.9	C13—C14—H14	118.6
C7—C2—C3	119.9 (3)	N3—C15—S1'	156.9 (9)
C7—C2—C1	118.0 (3)	N3—C15—S1	176.5 (3)
C3—C2—C1	122.1 (3)	S1'—C15—S1	26.5 (8)
O1—C3—C2	124.9 (3)	O3—C16—N4	126.1 (3)
O1—C3—C4	117.8 (3)	O3—C16—H16	116.9
C2—C3—C4	117.3 (3)	N4—C16—H16	116.9
O2—C4—C5	125.5 (3)	N4—C17—H17A	109.5
O2—C4—C3	113.9 (3)	N4—C17—H17B	109.5
C5—C4—C3	120.6 (3)	H17A—C17—H17B	109.5
C4—C5—C6	121.2 (3)	N4—C17—H17C	109.5
C4—C5—H5	119.4	H17A—C17—H17C	109.5
C6—C5—H5	119.4	H17B—C17—H17C	109.5
C7—C6—C5	119.8 (3)	N4—C18—H18A	109.5
C7—C6—H6	120.1	N4—C18—H18B	109.5
C5—C6—H6	120.1	H18A—C18—H18B	109.5
C6—C7—C2	121.2 (3)	N4—C18—H18C	109.5
C6—C7—H7	119.4	H18A—C18—H18C	109.5
C2—C7—H7	119.4	H18B—C18—H18C	109.5
O2—C8—H8A	109.5

Experimental details

Crystal data
Chemical formula	[Cu(C₁₄H₁₃N₂O₂)(NCS)(C₃H₇NO)]
M_r	435.98
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.6768 (9), 10.9310 (11), 11.0689 (12)
α, β, γ (°)	83.251 (2), 72.023 (1), 79.530 (1)
V (Å³)	979.84 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.25
Crystal size (mm)	0.20 × 0.12 × 0.09

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.737, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	5129, 3392, 2679
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.090, 1.09
No. of reflections	3392
No. of parameters	251
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.37

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—O1	1.905 (2)	Cu1—N2	2.012 (2)
Cu1—N1	1.942 (2)	Cu1—O3	2.392 (2)
Cu1—N3	1.971 (3)

O1—Cu1—N1	92.88 (9)	N3—Cu1—N2	94.01 (10)
O1—Cu1—N3	90.19 (9)	O1—Cu1—O3	93.96 (8)
N1—Cu1—N3	168.56 (9)	N1—Cu1—O3	96.07 (8)
O1—Cu1—N2	173.84 (9)	N3—Cu1—O3	94.71 (9)
N1—Cu1—N2	82.13 (10)	N2—Cu1—O3	90.18 (8)

References

Li, Z.-X. & Zhang, X.-L. (2004). Acta Cryst. E60, m1017–m1019. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Pointeau, P., Patin, H., Mousser, A. & le Marouile, J.-Y. (1986). J. Organomet. Chem. 312, 263–276. CSD CrossRef CAS Web of Science Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
You, Z.-L. & Zhu, H.-L. (2004). Z. Anorg. Allg. Chem. 630, 2754–2760. Web of Science CSD CrossRef CAS Google Scholar

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