Tetra-μ-acetato-κ8O:O′-bis­{[2-(m-tolyl­amino)pyridine-κN]copper(II)}

Fairuz, Z.A.; Aiyub, Z.; Abdullah, Z.; Ng, S.W.

doi:10.1107/S1600536809050041

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1690

doi:10.1107/S1600536809050041

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Tetra-μ-acetato-κ⁸O:O′-bis{[2-(m-tolylamino)pyridine-κN]copper(II)}

Zainal Abidin Fairuz,^a Zaharah Aiyub,^a Zanariah Abdullah ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 20 November 2009; accepted 20 November 2009; online 28 November 2009)

In the crystal structure of the title compound, [Cu₂(C₂H₃O₂)₄(C₁₂H₁₂N₂)₂], the binuclear molecule lies about a center of inversion; the four acetate groups each bridge a pair of Cu^II atoms. The coordination of the metal atom is distorted square-pyramidal, with the bonding O atoms comprising a square basal plane and the coordinating N atom of the N-heterocycle occupying the apical position. The pyridine ring is twisted with respect to the benzene ring at a dihedral angle of 45.68 (16)°. Intramolecular N—H⋯O hydrogen bonding is present between the imino and carboxy groups.

Related literature

There are many examples of tetrakisacetatobis[(substituted pyridine)copper] complexes. For examples of 2-aminopyridyl derivatives, see: Barquín et al. (2004 ); Seco et al. (2004 ); Sieroń (2004 ).

Experimental

Crystal data

[Cu₂(C₂H₃O₂)₄(C₁₂H₁₂N₂)₂]
M_r = 731.73
Triclinic, $[P \overline 1]$
a = 7.7143 (2) Å
b = 10.5625 (3) Å
c = 11.2413 (3) Å
α = 66.531 (2)°
β = 85.740 (2)°
γ = 78.568 (2)°
V = 823.51 (4) Å³
Z = 1
Mo Kα radiation
μ = 1.35 mm⁻¹
T = 293 K
0.25 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.730, T_max = 0.936
6451 measured reflections
3678 independent reflections
2915 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.098
S = 1.07
3678 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.9762 (19)
Cu1—O2ⁱ	1.9866 (19)
Cu1—O3	1.967 (2)
Cu1—O4ⁱ	1.966 (2)
Cu1—N1	2.197 (2)
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—H2⋯O2ⁱ	0.86	2.17	2.913 (3)	145
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050041/xu2688sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050041/xu2688Isup2.hkl

checkCIF report

Related literature top

There are many examples of tetrakisacetatobis[(substituted pyridine)copper] complexes. For examples of 2-aminopyridyl derivatives, see: Barquín et al. (2004); Seco et al. (2004); Sieroń (2004).

Experimental top

Copper acetate (0.1 g, 0.5 mmol) was dissolved in acetonitrile (5 ml). The solution was mixed with a solution of 3-tolylamino-2-pyridine (0.2 g, 1.1 mmol) dissolved in acetonitrile (15 ml). The green precipitate that formed was recrystallized from acetonitrile.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Cu₂(C₂H₃O₂)₄(C₁₂H₁₂N₂)₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. Dashed lines indicate the hydrogen bonding.

Tetra-µ-acetato-κ⁸O:O'-bis{[2-(m-tolylamino)pyridine- κN]copper(II)} top

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₂H₁₂N₂)₂]	Z = 1
M_r = 731.73	F(000) = 378
Triclinic, P1	D_x = 1.475 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7143 (2) Å	Cell parameters from 2561 reflections
b = 10.5625 (3) Å	θ = 2.3–27.6°
c = 11.2413 (3) Å	µ = 1.35 mm⁻¹
α = 66.531 (2)°	T = 293 K
β = 85.740 (2)°	Prism, green
γ = 78.568 (2)°	0.25 × 0.15 × 0.05 mm
V = 823.51 (4) Å³

Data collection top

Bruker SMART APEX diffractometer	3678 independent reflections
Radiation source: fine-focus sealed tube	2915 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.730, T_max = 0.936	k = −13→13
6451 measured reflections	l = −14→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0426P)² + 0.4239P] where P = (F_o² + 2F_c²)/3
3678 reflections	(Δ/σ)_max = 0.001
211 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₂H₁₂N₂)₂]	γ = 78.568 (2)°
M_r = 731.73	V = 823.51 (4) Å³
Triclinic, P1	Z = 1
a = 7.7143 (2) Å	Mo Kα radiation
b = 10.5625 (3) Å	µ = 1.35 mm⁻¹
c = 11.2413 (3) Å	T = 293 K
α = 66.531 (2)°	0.25 × 0.15 × 0.05 mm
β = 85.740 (2)°

Data collection top

Bruker SMART APEX diffractometer	3678 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2915 reflections with I > 2σ(I)
T_min = 0.730, T_max = 0.936	R_int = 0.023
6451 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.07	Δρ_max = 0.49 e Å⁻³
3678 reflections	Δρ_min = −0.59 e Å⁻³
211 parameters

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

	x	y	z	U_iso*/U_eq
Cu1	0.58894 (4)	0.46743 (4)	0.60797 (3)	0.03044 (12)
O1	0.6955 (3)	0.6324 (2)	0.50147 (18)	0.0439 (5)
O2	0.5505 (3)	0.6857 (2)	0.31997 (18)	0.0419 (5)
O3	0.7582 (3)	0.3494 (2)	0.53769 (19)	0.0460 (5)
O4	0.6100 (3)	0.4052 (2)	0.35536 (19)	0.0436 (5)
N1	0.7506 (3)	0.4120 (2)	0.7806 (2)	0.0304 (5)
N2	0.5409 (3)	0.3175 (3)	0.9254 (2)	0.0446 (6)
H2	0.4771	0.3436	0.8573	0.053*
C1	0.6579 (4)	0.7076 (3)	0.3856 (3)	0.0342 (6)
C2	0.7467 (5)	0.8317 (4)	0.3197 (3)	0.0570 (9)
H2A	0.8448	0.8237	0.3717	0.085*
H2B	0.6637	0.9162	0.3091	0.085*
H2C	0.7885	0.8346	0.2363	0.085*
C3	0.7354 (4)	0.3375 (3)	0.4329 (3)	0.0378 (6)
C4	0.8709 (5)	0.2335 (4)	0.4000 (3)	0.0578 (9)
H4A	0.9175	0.1573	0.4784	0.087*
H4B	0.9652	0.2787	0.3520	0.087*
H4C	0.8169	0.1979	0.3485	0.087*
C5	0.9143 (4)	0.4436 (3)	0.7539 (3)	0.0389 (7)
H5	0.9471	0.4835	0.6675	0.047*
C6	1.0348 (4)	0.4198 (3)	0.8479 (3)	0.0438 (7)
H6	1.1454	0.4446	0.8259	0.053*
C7	0.9871 (4)	0.3582 (3)	0.9752 (3)	0.0403 (7)
H7	1.0662	0.3400	1.0411	0.048*
C8	0.8228 (4)	0.3236 (3)	1.0051 (3)	0.0395 (7)
H8	0.7896	0.2817	1.0912	0.047*
C9	0.7059 (3)	0.3518 (3)	0.9053 (2)	0.0309 (6)
C10	0.4629 (4)	0.2444 (3)	1.0447 (2)	0.0339 (6)
C11	0.3760 (4)	0.1388 (3)	1.0512 (3)	0.0365 (6)
H11	0.3785	0.1149	0.9799	0.044*
C12	0.2858 (4)	0.0682 (3)	1.1613 (3)	0.0417 (7)
C13	0.2886 (5)	0.1024 (4)	1.2678 (3)	0.0513 (8)
H13	0.2327	0.0539	1.3440	0.062*
C14	0.3736 (5)	0.2078 (4)	1.2618 (3)	0.0522 (8)
H14	0.3734	0.2302	1.3339	0.063*
C15	0.4592 (4)	0.2808 (3)	1.1506 (3)	0.0420 (7)
H15	0.5137	0.3533	1.1468	0.050*
C16	0.1823 (5)	−0.0390 (4)	1.1628 (4)	0.0658 (10)
H16A	0.2210	−0.0685	1.0932	0.099*
H16B	0.0587	0.0016	1.1522	0.099*
H16C	0.2012	−0.1187	1.2440	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02917 (19)	0.0399 (2)	0.02439 (17)	−0.01136 (14)	0.00032 (12)	−0.01252 (14)
O1	0.0492 (13)	0.0523 (13)	0.0312 (10)	−0.0263 (10)	−0.0027 (9)	−0.0090 (9)
O2	0.0452 (12)	0.0516 (13)	0.0325 (10)	−0.0246 (10)	−0.0018 (9)	−0.0125 (9)
O3	0.0414 (12)	0.0601 (14)	0.0384 (11)	−0.0004 (10)	−0.0021 (9)	−0.0250 (10)
O4	0.0412 (12)	0.0558 (13)	0.0376 (11)	−0.0023 (10)	−0.0020 (9)	−0.0251 (10)
N1	0.0282 (12)	0.0365 (13)	0.0277 (11)	−0.0101 (10)	−0.0003 (9)	−0.0118 (10)
N2	0.0374 (14)	0.0714 (18)	0.0249 (11)	−0.0241 (13)	−0.0002 (10)	−0.0123 (12)
C1	0.0330 (15)	0.0411 (16)	0.0309 (14)	−0.0141 (12)	0.0046 (11)	−0.0138 (12)
C2	0.065 (2)	0.058 (2)	0.0484 (19)	−0.0362 (19)	−0.0014 (16)	−0.0094 (16)
C3	0.0370 (16)	0.0418 (17)	0.0353 (15)	−0.0110 (13)	0.0082 (12)	−0.0154 (13)
C4	0.058 (2)	0.062 (2)	0.051 (2)	0.0063 (18)	0.0032 (16)	−0.0289 (18)
C5	0.0349 (16)	0.0487 (18)	0.0323 (14)	−0.0123 (14)	0.0022 (12)	−0.0133 (13)
C6	0.0298 (15)	0.0532 (19)	0.0489 (18)	−0.0094 (14)	−0.0038 (13)	−0.0191 (15)
C7	0.0344 (16)	0.0476 (18)	0.0387 (16)	−0.0007 (13)	−0.0117 (12)	−0.0179 (14)
C8	0.0398 (17)	0.0489 (18)	0.0277 (14)	−0.0074 (14)	−0.0039 (12)	−0.0125 (13)
C9	0.0293 (14)	0.0353 (15)	0.0289 (13)	−0.0068 (11)	−0.0014 (10)	−0.0129 (11)
C10	0.0299 (14)	0.0421 (16)	0.0272 (13)	−0.0056 (12)	0.0013 (10)	−0.0117 (12)
C11	0.0327 (15)	0.0406 (16)	0.0362 (15)	−0.0027 (12)	0.0003 (11)	−0.0171 (13)
C12	0.0366 (16)	0.0317 (16)	0.0494 (18)	−0.0040 (13)	0.0041 (13)	−0.0100 (13)
C13	0.052 (2)	0.055 (2)	0.0358 (16)	−0.0099 (16)	0.0131 (14)	−0.0090 (15)
C14	0.058 (2)	0.068 (2)	0.0357 (16)	−0.0142 (18)	0.0102 (14)	−0.0261 (16)
C15	0.0450 (18)	0.0476 (18)	0.0385 (16)	−0.0129 (15)	0.0054 (13)	−0.0210 (14)
C16	0.065 (3)	0.047 (2)	0.080 (3)	−0.0220 (19)	0.006 (2)	−0.0163 (19)

Geometric parameters (Å, º) top

Cu1—O1	1.9762 (19)	C4—H4C	0.9600
Cu1—O2ⁱ	1.9866 (19)	C5—C6	1.372 (4)
Cu1—O3	1.967 (2)	C5—H5	0.9300
Cu1—O4ⁱ	1.966 (2)	C6—C7	1.372 (4)
Cu1—N1	2.197 (2)	C6—H6	0.9300
Cu1—Cu1ⁱ	2.6532 (6)	C7—C8	1.370 (4)
O1—C1	1.246 (3)	C7—H7	0.9300
O2—C1	1.259 (3)	C8—C9	1.393 (4)
O2—Cu1ⁱ	1.9866 (19)	C8—H8	0.9300
O3—C3	1.261 (3)	C10—C11	1.387 (4)
O4—C3	1.250 (4)	C10—C15	1.385 (4)
O4—Cu1ⁱ	1.966 (2)	C11—C12	1.384 (4)
N1—C9	1.339 (3)	C11—H11	0.9300
N1—C5	1.352 (3)	C12—C13	1.385 (4)
N2—C9	1.370 (3)	C12—C16	1.503 (4)
N2—C10	1.413 (3)	C13—C14	1.377 (5)
N2—H2	0.8600	C13—H13	0.9300
C1—C2	1.498 (4)	C14—C15	1.380 (4)
C2—H2A	0.9600	C14—H14	0.9300
C2—H2B	0.9600	C15—H15	0.9300
C2—H2C	0.9600	C16—H16A	0.9600
C3—C4	1.500 (4)	C16—H16B	0.9600
C4—H4A	0.9600	C16—H16C	0.9600
C4—H4B	0.9600

O4ⁱ—Cu1—O3	167.64 (8)	H4A—C4—H4C	109.5
O4ⁱ—Cu1—O1	88.77 (9)	H4B—C4—H4C	109.5
O3—Cu1—O1	90.33 (9)	N1—C5—C6	123.4 (3)
O4ⁱ—Cu1—O2ⁱ	89.16 (9)	N1—C5—H5	118.3
O3—Cu1—O2ⁱ	89.01 (9)	C6—C5—H5	118.3
O1—Cu1—O2ⁱ	167.27 (8)	C5—C6—C7	118.1 (3)
O4ⁱ—Cu1—N1	98.40 (8)	C5—C6—H6	121.0
O3—Cu1—N1	93.96 (8)	C7—C6—H6	121.0
O1—Cu1—N1	94.60 (8)	C8—C7—C6	119.8 (3)
O2ⁱ—Cu1—N1	98.13 (8)	C8—C7—H7	120.1
O4ⁱ—Cu1—Cu1ⁱ	84.47 (6)	C6—C7—H7	120.1
O3—Cu1—Cu1ⁱ	83.19 (6)	C7—C8—C9	119.3 (3)
O1—Cu1—Cu1ⁱ	83.69 (6)	C7—C8—H8	120.3
O2ⁱ—Cu1—Cu1ⁱ	83.61 (6)	C9—C8—H8	120.3
N1—Cu1—Cu1ⁱ	176.65 (6)	N1—C9—N2	115.0 (2)
C1—O1—Cu1	124.57 (18)	N1—C9—C8	121.4 (2)
C1—O2—Cu1ⁱ	123.80 (18)	N2—C9—C8	123.6 (2)
C3—O3—Cu1	124.0 (2)	C11—C10—C15	119.4 (3)
C3—O4—Cu1ⁱ	122.82 (18)	C11—C10—N2	117.7 (2)
C9—N1—C5	118.0 (2)	C15—C10—N2	122.7 (3)
C9—N1—Cu1	127.85 (17)	C10—C11—C12	121.6 (3)
C5—N1—Cu1	114.18 (17)	C10—C11—H11	119.2
C9—N2—C10	127.9 (2)	C12—C11—H11	119.2
C9—N2—H2	116.1	C13—C12—C11	118.2 (3)
C10—N2—H2	116.1	C13—C12—C16	121.2 (3)
O1—C1—O2	124.3 (2)	C11—C12—C16	120.6 (3)
O1—C1—C2	117.9 (2)	C14—C13—C12	120.5 (3)
O2—C1—C2	117.8 (3)	C14—C13—H13	119.8
C1—C2—H2A	109.5	C12—C13—H13	119.8
C1—C2—H2B	109.5	C13—C14—C15	121.2 (3)
H2A—C2—H2B	109.5	C13—C14—H14	119.4
C1—C2—H2C	109.5	C15—C14—H14	119.4
H2A—C2—H2C	109.5	C14—C15—C10	119.1 (3)
H2B—C2—H2C	109.5	C14—C15—H15	120.5
O4—C3—O3	125.3 (3)	C10—C15—H15	120.5
O4—C3—C4	118.0 (3)	C12—C16—H16A	109.5
O3—C3—C4	116.7 (3)	C12—C16—H16B	109.5
C3—C4—H4A	109.5	H16A—C16—H16B	109.5
C3—C4—H4B	109.5	C12—C16—H16C	109.5
H4A—C4—H4B	109.5	H16A—C16—H16C	109.5
C3—C4—H4C	109.5	H16B—C16—H16C	109.5

O4ⁱ—Cu1—O1—C1	−84.3 (2)	C9—N1—C5—C6	−1.4 (4)
O3—Cu1—O1—C1	83.4 (2)	Cu1—N1—C5—C6	178.8 (2)
O2ⁱ—Cu1—O1—C1	−3.6 (6)	N1—C5—C6—C7	1.3 (5)
N1—Cu1—O1—C1	177.4 (2)	C5—C6—C7—C8	−0.5 (5)
Cu1ⁱ—Cu1—O1—C1	0.3 (2)	C6—C7—C8—C9	−0.1 (5)
O4ⁱ—Cu1—O3—C3	0.2 (6)	C5—N1—C9—N2	−177.5 (3)
O1—Cu1—O3—C3	−85.6 (2)	Cu1—N1—C9—N2	2.2 (4)
O2ⁱ—Cu1—O3—C3	81.7 (2)	C5—N1—C9—C8	0.7 (4)
N1—Cu1—O3—C3	179.8 (2)	Cu1—N1—C9—C8	−179.6 (2)
Cu1ⁱ—Cu1—O3—C3	−2.0 (2)	C10—N2—C9—N1	175.0 (3)
O4ⁱ—Cu1—N1—C9	58.8 (2)	C10—N2—C9—C8	−3.2 (5)
O3—Cu1—N1—C9	−121.1 (2)	C7—C8—C9—N1	0.0 (4)
O1—Cu1—N1—C9	148.2 (2)	C7—C8—C9—N2	178.1 (3)
O2ⁱ—Cu1—N1—C9	−31.6 (2)	C9—N2—C10—C11	−134.6 (3)
O4ⁱ—Cu1—N1—C5	−121.5 (2)	C9—N2—C10—C15	50.2 (5)
O3—Cu1—N1—C5	58.6 (2)	C15—C10—C11—C12	−0.2 (4)
O1—Cu1—N1—C5	−32.0 (2)	N2—C10—C11—C12	−175.6 (3)
O2ⁱ—Cu1—N1—C5	148.2 (2)	C10—C11—C12—C13	−2.0 (4)
Cu1—O1—C1—O2	−2.2 (4)	C10—C11—C12—C16	175.8 (3)
Cu1—O1—C1—C2	178.1 (2)	C11—C12—C13—C14	2.4 (5)
Cu1ⁱ—O2—C1—O1	3.4 (4)	C16—C12—C13—C14	−175.4 (3)
Cu1ⁱ—O2—C1—C2	−176.9 (2)	C12—C13—C14—C15	−0.6 (5)
Cu1ⁱ—O4—C3—O3	−5.7 (4)	C13—C14—C15—C10	−1.6 (5)
Cu1ⁱ—O4—C3—C4	174.4 (2)	C11—C10—C15—C14	2.0 (4)
Cu1—O3—C3—O4	5.2 (4)	N2—C10—C15—C14	177.2 (3)
Cu1—O3—C3—C4	−175.0 (2)

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—H2···O2ⁱ	0.86	2.17	2.913 (3)	145

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₂H₃O₂)₄(C₁₂H₁₂N₂)₂]
M_r	731.73
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.7143 (2), 10.5625 (3), 11.2413 (3)
α, β, γ (°)	66.531 (2), 85.740 (2), 78.568 (2)
V (Å³)	823.51 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.35
Crystal size (mm)	0.25 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.730, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	6451, 3678, 2915
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.098, 1.07
No. of reflections	3678
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.59

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Cu1—O1	1.9762 (19)	Cu1—O4ⁱ	1.966 (2)
Cu1—O2ⁱ	1.9866 (19)	Cu1—N1	2.197 (2)
Cu1—O3	1.967 (2)

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—H2···O2ⁱ	0.86	2.17	2.913 (3)	145.0

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank the University of Malaya (grant No. RG027/09AFR, PS374/09 A) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Barquín, M., González Garmendia, M. J., Pacheco, S., Pinilla, E., Quintela, S., Seco, J. M. & Torres, M. R. (2004). Inorg. Chim. Acta, 357, 3230–3236. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Seco, J. M., González Garmendia, M. J., Pinilla, E. & Torres, M. R. (2004). Polyhedron, 21, 457–464. Web of Science CSD CrossRef 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
Sieroń, L. (2004). Acta Cryst. E60, m577–m578. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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Volume 65| Part 12| December 2009| Page m1690

doi:10.1107/S1600536809050041

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