Tetra-μ-acetato-κ8O:O′-bis­{[N-(4-methyl­phen­yl)pyridin-2-amine-κN1]copper(II)}(Cu—Cu)

Fairuz, Z.A.; Aiyub, Z.; Abdullah, Z.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811044333

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1636

doi:10.1107/S1600536811044333

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Tetra-μ-acetato-κ⁸O:O′-bis{[N-(4-methylphenyl)pyridin-2-amine-κN¹]copper(II)}(Cu—Cu)

Zainal Abidin Fairuz,^a Zaharah Aiyub,^a Zanariah Abdullah,^a ‡ Seik Weng Ng ^a,^b and Edward R. T. Tiekink ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 24 October 2011; accepted 25 October 2011; online 29 October 2011)

The complete dinuclear molecule of the title complex, [Cu₂(CH₃COO)₄(C₁₂H₁₂N₂)₂], is generated by a centre of inversion. The Cu^II atoms are connected [Cu—Cu = 2.6329 (16) Å] and bridged by four acetate ligands. The distorted octahedral coordination geometry is completed by a terminal pyridine N atom. The amine H atom forms an intramolecular N—H⋯O hydrogen bond.

Related literature

For related examples of tetrakisacetatobis[(substituted 2-aminopyridyl)copper] complexes, see: Fairuz et al. (2010a ,b ).

Experimental

Crystal data

[Cu₂(C₂H₃O₂)₄(C₁₂H₁₂N₂)₂]
M_r = 731.75
Monoclinic, P 2₁ /c
a = 7.6285 (9) Å
b = 11.3242 (13) Å
c = 18.566 (2) Å
β = 95.717 (2)°
V = 1595.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.39 mm⁻¹
T = 100 K
0.22 × 0.13 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.495, T_max = 0.862
11607 measured reflections
2806 independent reflections
2203 reflections with I > 2σ(I)
R_int = 0.103

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.209
S = 1.08
2806 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 1.31 e Å⁻³
Δρ_min = −1.29 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu—O2ⁱ	1.947 (5)
Cu—O1	1.950 (5)
Cu—O3	1.976 (5)
Cu—O4ⁱ	1.976 (5)
Cu—N1	2.205 (6)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O3	0.86	2.21	2.911 (8)	139

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811044333/hg5122sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044333/hg5122Isup2.hkl

checkCIF report

Comment top

The crystal structure of the title complex, (I), was investigated in connection with structural studies of tetrakisacetatobis[(substituted 2-aminopyridyl)copper(II)] complexes (Fairuz et al., 2010a; Fairuz et al., 2010b). The complex, Fig. 1, is centrosymmetric and feature four symmetrically bridging acetate ligands and two terminally connected pyridyl-N atoms. These define an NO₄ donor set and the distorted octahedral geometry is completed by a Cu atom, Table 1. The orientation of the N-p-tolylpyridin-2-amine ligand is such to enable the formation of an intramolecular N—H···O hydrogen bond, Table 2. The pyridyl-2-amine ligand is twisted with the dihedral angle between the pyridyl and benzene rings being 59.3 (4)°.

Related literature top

For related examples of tetrakisacetatobis[(substituted 2-aminopyridyl)copper] complexes, see: Fairuz et al. (2010a,b).

Experimental top

N-p-Tolylpyridin-2-amine (0.2 g, 1.1 mmol) was dissolved in acetonitrile (15 ml), added to trimethyl orthoformate (10 ml) and the mixture then heated to 50 °C. Copper acetate (0.1 g, 0.5 mmol) dissolved in acetonitrile (15 ml) was added to the solution. The green precipitate that formed, was collected and recrystallized from acetonitrile to give green crystals.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. The complex is centrosymmetric. The unlabelled atoms are related by the symmetry operation 1 - x, 1 - y, 1 - z.

Tetra-µ-acetato-κ⁸O:O'-bis{[N-(4- methylphenyl)pyridin-2-amine-κN¹]copper(II)}(Cu—Cu) top

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₂H₁₂N₂)₂]	F(000) = 756
M_r = 731.75	D_x = 1.523 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2708 reflections
a = 7.6285 (9) Å	θ = 2.7–23.1°
b = 11.3242 (13) Å	µ = 1.39 mm⁻¹
c = 18.566 (2) Å	T = 100 K
β = 95.717 (2)°	Prism, green
V = 1595.9 (3) Å³	0.22 × 0.13 × 0.05 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	2806 independent reflections
Radiation source: fine-focus sealed tube	2203 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.103
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.495, T_max = 0.862	k = −13→13
11607 measured reflections	l = −22→22

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.209	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0765P)² + 11.519P] where P = (F_o² + 2F_c²)/3
2806 reflections	(Δ/σ)_max = 0.004
211 parameters	Δρ_max = 1.31 e Å⁻³
0 restraints	Δρ_min = −1.29 e Å⁻³

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₂H₁₂N₂)₂]	V = 1595.9 (3) Å³
M_r = 731.75	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.6285 (9) Å	µ = 1.39 mm⁻¹
b = 11.3242 (13) Å	T = 100 K
c = 18.566 (2) Å	0.22 × 0.13 × 0.05 mm
β = 95.717 (2)°

Data collection top

Bruker SMART APEX diffractometer	2806 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2203 reflections with I > 2σ(I)
T_min = 0.495, T_max = 0.862	R_int = 0.103
11607 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.209	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0765P)² + 11.519P] where P = (F_o² + 2F_c²)/3
2806 reflections	Δρ_max = 1.31 e Å⁻³
211 parameters	Δρ_min = −1.29 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu	0.59639 (11)	0.59398 (7)	0.51769 (5)	0.0291 (3)
O1	0.7488 (7)	0.4818 (4)	0.5735 (3)	0.0422 (14)
O2	0.5861 (7)	0.3220 (5)	0.5427 (3)	0.0424 (14)
O3	0.4444 (7)	0.6035 (5)	0.5977 (3)	0.0408 (13)
O4	0.2853 (7)	0.4450 (5)	0.5692 (3)	0.0426 (14)
N1	0.7623 (8)	0.7488 (5)	0.5486 (3)	0.0301 (13)
N2	0.5402 (8)	0.8521 (6)	0.5941 (4)	0.0422 (17)
H2n	0.4726	0.7948	0.5785	0.051*
C1	0.7159 (9)	0.3738 (6)	0.5757 (4)	0.0323 (17)
C2	0.8381 (13)	0.2988 (8)	0.6240 (5)	0.052 (2)
H2A	0.8227	0.2158	0.6099	0.079*
H2B	0.8119	0.3085	0.6743	0.079*
H2C	0.9601	0.3227	0.6196	0.079*
C3	0.3262 (10)	0.5337 (6)	0.6077 (4)	0.0330 (17)
C4	0.2223 (13)	0.5545 (8)	0.6707 (5)	0.052 (2)
H4A	0.1985	0.6391	0.6750	0.078*
H4B	0.2897	0.5265	0.7151	0.078*
H4C	0.1105	0.5113	0.6633	0.078*
C5	0.9295 (9)	0.7373 (7)	0.5348 (4)	0.0377 (18)
H5	0.9643	0.6655	0.5139	0.045*
C6	1.0509 (10)	0.8218 (8)	0.5488 (5)	0.047 (2)
H6	1.1689	0.8111	0.5378	0.056*
C7	0.9980 (11)	0.9249 (7)	0.5798 (5)	0.047 (2)
H7	1.0804	0.9869	0.5903	0.057*
C8	0.8305 (10)	0.9382 (7)	0.5952 (5)	0.0388 (19)
H8	0.7948	1.0090	0.6170	0.047*
C9	0.7114 (9)	0.8485 (6)	0.5790 (4)	0.0292 (16)
C10	0.4654 (10)	0.9431 (7)	0.6335 (4)	0.0345 (17)
C11	0.4545 (10)	1.0572 (7)	0.6082 (4)	0.0374 (18)
H11	0.5019	1.0777	0.5644	0.045*
C12	0.3738 (10)	1.1416 (7)	0.6472 (4)	0.0395 (18)
H12	0.3673	1.2204	0.6296	0.047*
C13	0.3027 (10)	1.1160 (7)	0.7101 (4)	0.0376 (18)
C14	0.3148 (11)	0.9995 (8)	0.7341 (4)	0.045 (2)
H14	0.2649	0.9779	0.7771	0.054*
C15	0.3975 (11)	0.9159 (7)	0.6965 (5)	0.044 (2)
H15	0.4076	0.8375	0.7147	0.053*
C16	0.2120 (13)	1.2061 (9)	0.7533 (5)	0.058 (2)
H16A	0.2487	1.1952	0.8050	0.087*
H16B	0.0841	1.1961	0.7444	0.087*
H16C	0.2443	1.2857	0.7387	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.0282 (5)	0.0182 (5)	0.0409 (5)	−0.0059 (4)	0.0038 (3)	−0.0019 (4)
O1	0.034 (3)	0.023 (3)	0.068 (4)	0.000 (2)	−0.007 (3)	0.000 (2)
O2	0.042 (3)	0.023 (3)	0.060 (4)	−0.009 (2)	−0.004 (3)	0.006 (2)
O3	0.044 (3)	0.029 (3)	0.052 (3)	−0.009 (3)	0.017 (3)	−0.002 (2)
O4	0.039 (3)	0.033 (3)	0.058 (4)	−0.014 (3)	0.016 (3)	−0.011 (3)
N1	0.028 (3)	0.021 (3)	0.041 (3)	−0.009 (2)	0.002 (3)	0.001 (3)
N2	0.028 (3)	0.026 (3)	0.073 (5)	−0.008 (3)	0.007 (3)	−0.015 (3)
C1	0.027 (4)	0.019 (4)	0.052 (5)	−0.001 (3)	0.013 (3)	−0.003 (3)
C2	0.057 (6)	0.031 (5)	0.067 (6)	0.008 (4)	−0.005 (5)	0.000 (4)
C3	0.035 (4)	0.022 (4)	0.043 (4)	0.002 (3)	0.007 (3)	0.005 (3)
C4	0.058 (6)	0.040 (5)	0.062 (6)	−0.004 (4)	0.023 (5)	−0.005 (4)
C5	0.020 (4)	0.034 (4)	0.060 (5)	0.000 (3)	0.008 (3)	−0.005 (4)
C6	0.020 (4)	0.044 (5)	0.076 (6)	−0.008 (4)	0.004 (4)	−0.006 (4)
C7	0.033 (4)	0.035 (5)	0.073 (6)	−0.018 (4)	0.004 (4)	−0.007 (4)
C8	0.033 (4)	0.023 (4)	0.060 (5)	−0.003 (3)	0.000 (4)	−0.009 (3)
C9	0.034 (4)	0.017 (3)	0.036 (4)	−0.002 (3)	−0.002 (3)	−0.002 (3)
C10	0.031 (4)	0.025 (4)	0.047 (5)	−0.002 (3)	0.001 (3)	−0.008 (3)
C11	0.036 (4)	0.030 (4)	0.046 (5)	−0.011 (3)	0.008 (3)	0.000 (3)
C12	0.040 (4)	0.027 (4)	0.052 (5)	−0.002 (3)	0.003 (4)	0.004 (4)
C13	0.038 (4)	0.030 (4)	0.044 (4)	0.000 (3)	−0.006 (3)	−0.006 (3)
C14	0.054 (5)	0.040 (5)	0.044 (5)	0.007 (4)	0.016 (4)	0.009 (4)
C15	0.053 (5)	0.023 (4)	0.058 (5)	0.002 (4)	0.007 (4)	0.010 (4)
C16	0.060 (6)	0.048 (6)	0.067 (6)	0.009 (5)	0.005 (5)	−0.016 (5)

Geometric parameters (Å, º) top

Cu—O2ⁱ	1.947 (5)	C4—H4C	0.9800
Cu—O1	1.950 (5)	C5—C6	1.339 (11)
Cu—O3	1.976 (5)	C5—H5	0.9500
Cu—O4ⁱ	1.976 (5)	C6—C7	1.380 (12)
Cu—N1	2.205 (6)	C6—H6	0.9500
Cu—Cuⁱ	2.6329 (16)	C7—C8	1.345 (11)
O1—C1	1.249 (9)	C7—H7	0.9500
O2—C1	1.257 (9)	C8—C9	1.376 (10)
O2—Cuⁱ	1.947 (5)	C8—H8	0.9500
O3—C3	1.227 (9)	C10—C15	1.361 (11)
O4—C3	1.254 (9)	C10—C11	1.375 (11)
O4—Cuⁱ	1.976 (5)	C11—C12	1.381 (11)
N1—C5	1.332 (9)	C11—H11	0.9500
N1—C9	1.337 (9)	C12—C13	1.368 (11)
N2—C9	1.363 (10)	C12—H12	0.9500
N2—C10	1.417 (10)	C13—C14	1.393 (11)
N2—H2n	0.8600	C13—C16	1.508 (11)
C1—C2	1.494 (11)	C14—C15	1.368 (12)
C2—H2A	0.9800	C14—H14	0.9500
C2—H2B	0.9800	C15—H15	0.9500
C2—H2C	0.9800	C16—H16A	0.9800
C3—C4	1.496 (11)	C16—H16B	0.9800
C4—H4A	0.9800	C16—H16C	0.9800
C4—H4B	0.9800

O2ⁱ—Cu—O1	168.3 (2)	H4A—C4—H4C	109.5
O2ⁱ—Cu—O3	88.1 (2)	H4B—C4—H4C	109.5
O1—Cu—O3	90.0 (2)	N1—C5—C6	123.4 (8)
O2ⁱ—Cu—O4ⁱ	89.8 (3)	N1—C5—H5	118.3
O1—Cu—O4ⁱ	89.5 (3)	C6—C5—H5	118.3
O3—Cu—O4ⁱ	167.4 (2)	C5—C6—C7	117.4 (7)
O2ⁱ—Cu—N1	96.9 (2)	C5—C6—H6	121.3
O1—Cu—N1	94.8 (2)	C7—C6—H6	121.3
O3—Cu—N1	97.2 (2)	C8—C7—C6	120.5 (7)
O4ⁱ—Cu—N1	95.3 (2)	C8—C7—H7	119.8
O2ⁱ—Cu—Cuⁱ	84.36 (16)	C6—C7—H7	119.8
O1—Cu—Cuⁱ	83.94 (16)	C7—C8—C9	119.4 (7)
O3—Cu—Cuⁱ	82.90 (16)	C7—C8—H8	120.3
O4ⁱ—Cu—Cuⁱ	84.55 (16)	C9—C8—H8	120.3
N1—Cu—Cuⁱ	178.73 (17)	N1—C9—N2	115.8 (6)
C1—O1—Cu	122.9 (5)	N1—C9—C8	120.2 (7)
C1—O2—Cuⁱ	122.4 (5)	N2—C9—C8	124.0 (7)
C3—O3—Cu	125.0 (5)	C15—C10—C11	119.5 (7)
C3—O4—Cuⁱ	122.4 (5)	C15—C10—N2	119.1 (7)
C5—N1—C9	119.2 (6)	C11—C10—N2	121.3 (7)
C5—N1—Cu	114.1 (5)	C10—C11—C12	119.0 (7)
C9—N1—Cu	126.7 (5)	C10—C11—H11	120.5
C9—N2—C10	124.8 (6)	C12—C11—H11	120.5
C9—N2—H2n	117.6	C13—C12—C11	122.5 (7)
C10—N2—H2n	117.6	C13—C12—H12	118.7
O1—C1—O2	126.3 (7)	C11—C12—H12	118.7
O1—C1—C2	117.4 (7)	C12—C13—C14	117.0 (7)
O2—C1—C2	116.2 (7)	C12—C13—C16	123.6 (8)
C1—C2—H2A	109.5	C14—C13—C16	119.4 (8)
C1—C2—H2B	109.5	C15—C14—C13	120.8 (8)
H2A—C2—H2B	109.5	C15—C14—H14	119.6
C1—C2—H2C	109.5	C13—C14—H14	119.6
H2A—C2—H2C	109.5	C10—C15—C14	121.1 (7)
H2B—C2—H2C	109.5	C10—C15—H15	119.5
O3—C3—O4	125.1 (7)	C14—C15—H15	119.5
O3—C3—C4	118.2 (7)	C13—C16—H16A	109.5
O4—C3—C4	116.7 (7)	C13—C16—H16B	109.5
C3—C4—H4A	109.5	H16A—C16—H16B	109.5
C3—C4—H4B	109.5	C13—C16—H16C	109.5
H4A—C4—H4B	109.5	H16A—C16—H16C	109.5
C3—C4—H4C	109.5	H16B—C16—H16C	109.5

O2ⁱ—Cu—O1—C1	2.3 (16)	C9—N1—C5—C6	−1.1 (12)
O3—Cu—O1—C1	82.8 (6)	Cu—N1—C5—C6	179.3 (7)
O4ⁱ—Cu—O1—C1	−84.7 (6)	N1—C5—C6—C7	0.7 (14)
N1—Cu—O1—C1	−180.0 (6)	C5—C6—C7—C8	0.2 (14)
Cuⁱ—Cu—O1—C1	−0.1 (6)	C6—C7—C8—C9	−0.7 (14)
O2ⁱ—Cu—O3—C3	84.9 (6)	C5—N1—C9—N2	−177.6 (7)
O1—Cu—O3—C3	−83.6 (6)	Cu—N1—C9—N2	2.1 (9)
O4ⁱ—Cu—O3—C3	4.2 (15)	C5—N1—C9—C8	0.5 (11)
N1—Cu—O3—C3	−178.4 (6)	Cu—N1—C9—C8	−179.8 (5)
Cuⁱ—Cu—O3—C3	0.3 (6)	C10—N2—C9—N1	172.4 (7)
O2ⁱ—Cu—N1—C5	−125.9 (5)	C10—N2—C9—C8	−5.6 (13)
O1—Cu—N1—C5	54.6 (6)	C7—C8—C9—N1	0.3 (12)
O3—Cu—N1—C5	145.2 (5)	C7—C8—C9—N2	178.3 (8)
O4ⁱ—Cu—N1—C5	−35.4 (6)	C9—N2—C10—C15	−118.9 (9)
O2ⁱ—Cu—N1—C9	54.5 (6)	C9—N2—C10—C11	63.5 (11)
O1—Cu—N1—C9	−125.0 (6)	C15—C10—C11—C12	−0.3 (12)
O3—Cu—N1—C9	−34.5 (6)	N2—C10—C11—C12	177.3 (7)
O4ⁱ—Cu—N1—C9	145.0 (6)	C10—C11—C12—C13	−0.5 (12)
Cu—O1—C1—O2	1.2 (11)	C11—C12—C13—C14	0.0 (12)
Cu—O1—C1—C2	−176.5 (6)	C11—C12—C13—C16	−179.3 (8)
Cuⁱ—O2—C1—O1	−1.9 (11)	C12—C13—C14—C15	1.2 (12)
Cuⁱ—O2—C1—C2	175.9 (6)	C16—C13—C14—C15	−179.4 (8)
Cu—O3—C3—O4	1.0 (12)	C11—C10—C15—C14	1.6 (13)
Cu—O3—C3—C4	−179.5 (6)	N2—C10—C15—C14	−176.1 (8)
Cuⁱ—O4—C3—O3	−2.1 (11)	C13—C14—C15—C10	−2.0 (14)
Cuⁱ—O4—C3—C4	178.3 (6)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O3	0.86	2.21	2.911 (8)	139

Experimental details

Crystal data
Chemical formula	[Cu₂(C₂H₃O₂)₄(C₁₂H₁₂N₂)₂]
M_r	731.75
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.6285 (9), 11.3242 (13), 18.566 (2)
β (°)	95.717 (2)
V (Å³)	1595.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.39
Crystal size (mm)	0.22 × 0.13 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.495, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	11607, 2806, 2203
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.209, 1.08
No. of reflections	2806
No. of parameters	211
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0765P)² + 11.519P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.31, −1.29

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu—O2ⁱ	1.947 (5)	Cu—O4ⁱ	1.976 (5)
Cu—O1	1.950 (5)	Cu—N1	2.205 (6)
Cu—O3	1.976 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O3	0.86	2.21	2.911 (8)	139

Footnotes

‡Additional correspondence author, e-mail: zana@um.edu.my.

Acknowledgements

We thank the University of Malaya (grant No. RG027/09AFR) for supporting this study.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fairuz, Z. A., Aiyub, Z., Abdullah, Z., Ng, S. W. & Tiekink, E. R. T. (2010a). Acta Cryst. E66, m1049–m1050. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fairuz, Z. A., Aiyub, Z., Abdullah, Z., Ng, S. W. & Tiekink, E. R. T. (2010b). Acta Cryst. E66, m1077–m1078. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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