Bis{μ-N′-[1-(5-bromo-2-oxidophen­yl)ethyl­idene]benzene­sulfono­hydrazidato}-κ3O2,N′:N;κ3N:O2,N′-bis­[(dimethyl sulfoxide-κO)copper(II)]

Ali, H.M.; Laila, M.; Rizal, R.M.; Ng, S.W.

doi:10.1107/S1600536808002201

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m414

doi:10.1107/S1600536808002201

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Bis{μ-N′-[1-(5-bromo-2-oxidophenyl)ethylidene]benzenesulfonohydrazidato}-κ³O²,N′:N;κ³N:O²,N′-bis[(dimethyl sulfoxide-κO)copper(II)]

Hapipah M. Ali,^a Musalem Laila,^a Razali M. Rizal ^a and Seik Weng Ng ^a ^*

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

(Received 7 January 2008; accepted 21 January 2008; online 25 January 2008)

In the title centrosymmetric dinuclear complex, [Cu₂(C₁₅H₁₁BrN₂O₃S)₂(C₂H₆OS)₂], the Cu^II ion is N,O-chelated by a dianionic ligand, monocoordinated by the sulfonamide N atom of a symmetry-related ligand and coordinated by an O atom from a dimethyl sulfoxide ligand, forming a distorted square-planar coordination geometry.

Related literature

For the structure of 2′-[1-(2-hydroxyphenyl)ethylidene]benzenesulfonohydrazide, see: Ali et al. (2007 ).

Experimental

Crystal data

[Cu₂(C₁₅H₁₁BrN₂O₃S)₂(C₂H₆OS)₂]
M_r = 1017.77
Triclinic, $[P \overline 1]$
a = 8.0831 (1) Å
b = 10.4972 (2) Å
c = 12.9481 (2) Å
α = 68.157 (1)°
β = 74.928 (1)°
γ = 70.691 (1)°
V = 950.56 (3) Å³
Z = 1
Mo Kα radiation
μ = 3.49 mm⁻¹
T = 123 (2) K
0.40 × 0.31 × 0.20 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.335, T_max = 0.542 (expected range = 0.308–0.497)
12330 measured reflections
4318 independent reflections
3788 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.151
S = 1.21
4318 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 1.75 e Å⁻³
Δρ_min = −0.89 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.894 (3)
Cu1—O4	1.986 (3)
Cu1—N1	1.967 (3)
Cu1—N2ⁱ	2.026 (3)
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002201/lh2588sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002201/lh2588Isup2.hkl

checkCIF report

Related literature top

For the structure of 2'-[1-(2-hydroxyphenyl)ethylidene]benzenesulfonohydrazide, see: Ali et al. (2007).

Experimental top

The Schiff base ligand was synthesized by refluxing 5-bromo-2-hydroxyacetophenone (0.6 g, 2.8 mmol) with benzene sulfonohydrazide (0.48 g,2.8 mmol)in ethanol for 2 h. The ligand then was refluxed with Copper (II) acetate for 5 h. The brown crystal were obtained by recrystalization the product from DMSO.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2008).

Figures top

Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level, and H atoms shown as spheres of arbitrary radii [symmetry code: (i) -x + 2, -y + 1, -z].

Bis{µ-N'-[1-(5-bromo-2- oxidophenyl)ethylidene]benzenesulfonohydrazidato}- κ³O²,N':N;κ³N:N',O²-bis[(dimethyl sulfoxide-κO)copper(II)] top

Crystal data top

[Cu₂(C₁₅H₁₁BrN₂O₃S)₂(C₂H₆OS)₂]	Z = 1
M_r = 1017.77	F(000) = 510
Triclinic, P1	D_x = 1.778 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0831 (1) Å	Cell parameters from 7546 reflections
b = 10.4972 (2) Å	θ = 2.7–31.0°
c = 12.9481 (2) Å	µ = 3.49 mm⁻¹
α = 68.157 (1)°	T = 123 K
β = 74.928 (1)°	Block, green
γ = 70.691 (1)°	0.40 × 0.31 × 0.20 mm
V = 950.56 (3) Å³

Data collection top

Bruker APEXII diffractometer	4318 independent reflections
Radiation source: medium-focus sealed tube	3788 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.335, T_max = 0.542	k = −13→13
12330 measured reflections	l = −16→16

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.21	w = 1/[σ²(F_o²) + (0.0827P)² + 1.8365P] where P = (F_o² + 2F_c²)/3
4318 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 1.75 e Å⁻³
0 restraints	Δρ_min = −0.89 e Å⁻³

Crystal data top

[Cu₂(C₁₅H₁₁BrN₂O₃S)₂(C₂H₆OS)₂]	γ = 70.691 (1)°
M_r = 1017.77	V = 950.56 (3) Å³
Triclinic, P1	Z = 1
a = 8.0831 (1) Å	Mo Kα radiation
b = 10.4972 (2) Å	µ = 3.49 mm⁻¹
c = 12.9481 (2) Å	T = 123 K
α = 68.157 (1)°	0.40 × 0.31 × 0.20 mm
β = 74.928 (1)°

Data collection top

Bruker APEXII diffractometer	4318 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3788 reflections with I > 2σ(I)
T_min = 0.335, T_max = 0.542	R_int = 0.027
12330 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.21	Δρ_max = 1.75 e Å⁻³
4318 reflections	Δρ_min = −0.89 e Å⁻³
238 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.33316 (6)	0.23924 (5)	0.54963 (4)	0.03789 (17)
Cu1	1.09563 (6)	0.32031 (5)	0.10740 (4)	0.02020 (15)
S1	1.13219 (13)	0.63204 (10)	0.05283 (8)	0.0213 (2)
S2	1.41379 (13)	0.06832 (10)	0.18255 (8)	0.0230 (2)
O1	1.0528 (4)	0.2167 (3)	0.2622 (3)	0.0285 (6)
O2	1.2628 (4)	0.4956 (3)	0.0677 (3)	0.0278 (6)
O3	1.1615 (4)	0.7489 (3)	−0.0472 (3)	0.0292 (7)
O4	1.3150 (4)	0.1704 (3)	0.0840 (2)	0.0253 (6)
N1	0.9142 (4)	0.4879 (3)	0.1354 (3)	0.0195 (6)
N2	0.9352 (4)	0.6205 (3)	0.0558 (3)	0.0198 (6)
C1	0.8917 (5)	0.2298 (4)	0.3191 (3)	0.0219 (8)
C2	0.8558 (6)	0.1098 (5)	0.4082 (3)	0.0269 (9)
H2	0.9472	0.0236	0.4212	0.032*
C3	0.6946 (6)	0.1120 (5)	0.4770 (3)	0.0274 (9)
H3	0.6759	0.0294	0.5370	0.033*
C4	0.5591 (6)	0.2368 (5)	0.4575 (3)	0.0249 (8)
C5	0.5843 (5)	0.3557 (4)	0.3695 (4)	0.0243 (8)
H5	0.4889	0.4393	0.3569	0.029*
C6	0.7481 (5)	0.3565 (4)	0.2975 (3)	0.0208 (7)
C7	0.7691 (5)	0.4889 (4)	0.2075 (3)	0.0217 (8)
C8	0.6221 (7)	0.6230 (5)	0.1999 (5)	0.0392 (12)
H8A	0.6631	0.7033	0.1428	0.059*
H8B	0.5875	0.6396	0.2731	0.059*
H8C	0.5198	0.6135	0.1788	0.059*
C10	1.1190 (5)	0.6831 (4)	0.1713 (3)	0.0220 (8)
C11	1.1381 (6)	0.5793 (5)	0.2752 (4)	0.0269 (8)
H11	1.1558	0.4822	0.2833	0.032*
C12	1.1307 (6)	0.6200 (5)	0.3673 (4)	0.0318 (9)
H12	1.1418	0.5505	0.4393	0.038*
C13	1.1072 (6)	0.7618 (5)	0.3547 (4)	0.0327 (10)
H13	1.1064	0.7884	0.4174	0.039*
C14	1.0849 (6)	0.8649 (5)	0.2507 (4)	0.0304 (9)
H14	1.0656	0.9622	0.2429	0.036*
C15	1.0910 (6)	0.8258 (4)	0.1583 (4)	0.0249 (8)
H15	1.0761	0.8957	0.0869	0.030*
C16	1.6285 (6)	0.0005 (5)	0.1132 (4)	0.0294 (9)
H16A	1.6190	−0.0542	0.0690	0.044*
H16B	1.7060	−0.0613	0.1694	0.044*
H16C	1.6786	0.0797	0.0631	0.044*
C17	1.4719 (6)	0.1775 (5)	0.2371 (4)	0.0310 (9)
H17A	1.3669	0.2215	0.2823	0.046*
H17B	1.5168	0.2519	0.1746	0.046*
H17C	1.5640	0.1193	0.2844	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0284 (3)	0.0359 (3)	0.0357 (3)	−0.01063 (19)	0.00829 (19)	−0.0030 (2)
Cu1	0.0171 (3)	0.0210 (3)	0.0222 (3)	−0.00342 (18)	−0.00075 (18)	−0.00929 (19)
S1	0.0190 (5)	0.0249 (5)	0.0240 (5)	−0.0098 (4)	0.0014 (3)	−0.0118 (4)
S2	0.0192 (5)	0.0238 (5)	0.0253 (5)	−0.0066 (4)	−0.0020 (4)	−0.0070 (4)
O1	0.0205 (14)	0.0309 (15)	0.0248 (14)	0.0000 (12)	−0.0005 (11)	−0.0063 (12)
O2	0.0179 (14)	0.0312 (16)	0.0391 (17)	−0.0064 (12)	0.0007 (12)	−0.0200 (13)
O3	0.0320 (17)	0.0352 (16)	0.0255 (15)	−0.0200 (14)	0.0015 (13)	−0.0095 (13)
O4	0.0220 (14)	0.0278 (14)	0.0245 (14)	0.0011 (11)	−0.0040 (11)	−0.0130 (12)
N1	0.0206 (16)	0.0187 (15)	0.0205 (15)	−0.0074 (12)	−0.0020 (12)	−0.0063 (12)
N2	0.0201 (16)	0.0205 (15)	0.0214 (15)	−0.0094 (12)	−0.0014 (12)	−0.0074 (12)
C1	0.0202 (18)	0.0271 (19)	0.0204 (18)	−0.0047 (15)	−0.0025 (14)	−0.0113 (15)
C2	0.030 (2)	0.0246 (19)	0.0213 (19)	0.0012 (16)	−0.0058 (16)	−0.0085 (15)
C3	0.036 (2)	0.0252 (19)	0.0199 (18)	−0.0089 (17)	−0.0040 (17)	−0.0047 (15)
C4	0.024 (2)	0.029 (2)	0.0213 (18)	−0.0088 (16)	0.0002 (15)	−0.0081 (16)
C5	0.0196 (18)	0.0247 (19)	0.028 (2)	−0.0055 (15)	−0.0014 (15)	−0.0090 (16)
C6	0.0190 (18)	0.0193 (17)	0.0245 (18)	−0.0061 (14)	−0.0008 (15)	−0.0081 (14)
C7	0.0190 (18)	0.0202 (18)	0.0255 (19)	−0.0070 (14)	0.0012 (15)	−0.0084 (15)
C8	0.030 (2)	0.021 (2)	0.046 (3)	−0.0012 (18)	0.011 (2)	−0.0033 (19)
C10	0.0177 (18)	0.0252 (19)	0.0275 (19)	−0.0056 (15)	−0.0009 (15)	−0.0149 (16)
C11	0.025 (2)	0.026 (2)	0.029 (2)	−0.0045 (16)	−0.0016 (16)	−0.0115 (16)
C12	0.029 (2)	0.038 (2)	0.027 (2)	−0.0038 (19)	−0.0042 (17)	−0.0122 (18)
C13	0.030 (2)	0.044 (3)	0.032 (2)	−0.0112 (19)	−0.0001 (18)	−0.023 (2)
C14	0.030 (2)	0.030 (2)	0.037 (2)	−0.0118 (18)	0.0038 (18)	−0.0194 (19)
C15	0.024 (2)	0.0241 (19)	0.027 (2)	−0.0099 (16)	0.0023 (16)	−0.0099 (16)
C16	0.023 (2)	0.027 (2)	0.038 (2)	−0.0021 (16)	−0.0020 (17)	−0.0153 (18)
C17	0.031 (2)	0.038 (2)	0.031 (2)	−0.0086 (19)	−0.0062 (18)	−0.0181 (19)

Geometric parameters (Å, º) top

Br1—C4	1.902 (4)	C5—H5	0.9500
Cu1—O1	1.894 (3)	C6—C7	1.472 (5)
Cu1—O4	1.986 (3)	C7—C8	1.501 (6)
Cu1—N1	1.967 (3)	C8—H8A	0.9800
Cu1—N2ⁱ	2.026 (3)	C8—H8B	0.9800
S1—O3	1.445 (3)	C8—H8C	0.9800
S1—O2	1.450 (3)	C10—C11	1.388 (6)
S1—N2	1.626 (3)	C10—C15	1.390 (6)
S1—C10	1.772 (4)	C11—C12	1.391 (6)
S2—O4	1.537 (3)	C11—H11	0.9500
S2—C17	1.779 (4)	C12—C13	1.387 (7)
S2—C16	1.781 (4)	C12—H12	0.9500
O1—C1	1.310 (5)	C13—C14	1.389 (7)
N1—C7	1.295 (5)	C13—H13	0.9500
N1—N2	1.423 (4)	C14—C15	1.388 (6)
N2—Cu1ⁱ	2.026 (3)	C14—H14	0.9500
C1—C2	1.410 (6)	C15—H15	0.9500
C1—C6	1.438 (5)	C16—H16A	0.9800
C2—C3	1.372 (6)	C16—H16B	0.9800
C2—H2	0.9500	C16—H16C	0.9800
C3—C4	1.388 (6)	C17—H17A	0.9800
C3—H3	0.9500	C17—H17B	0.9800
C4—C5	1.374 (6)	C17—H17C	0.9800
C5—C6	1.407 (6)

O1—Cu1—N1	89.77 (13)	C1—C6—C7	122.5 (4)
O1—Cu1—O4	91.02 (13)	N1—C7—C6	119.4 (3)
N1—Cu1—O4	167.44 (13)	N1—C7—C8	120.8 (4)
O1—Cu1—N2ⁱ	153.28 (14)	C6—C7—C8	119.7 (4)
N1—Cu1—N2ⁱ	93.89 (13)	C7—C8—H8A	109.5
O4—Cu1—N2ⁱ	91.03 (13)	C7—C8—H8B	109.5
O3—S1—O2	118.67 (19)	H8A—C8—H8B	109.5
O3—S1—N2	105.18 (18)	C7—C8—H8C	109.5
O2—S1—N2	112.07 (17)	H8A—C8—H8C	109.5
O3—S1—C10	107.86 (19)	H8B—C8—H8C	109.5
O2—S1—C10	106.05 (19)	C11—C10—C15	121.3 (4)
N2—S1—C10	106.37 (18)	C11—C10—S1	119.2 (3)
O4—S2—C17	105.9 (2)	C15—C10—S1	119.5 (3)
O4—S2—C16	102.9 (2)	C10—C11—C12	118.8 (4)
C17—S2—C16	98.1 (2)	C10—C11—H11	120.6
C1—O1—Cu1	121.3 (3)	C12—C11—H11	120.6
S2—O4—Cu1	120.97 (17)	C13—C12—C11	120.3 (4)
C7—N1—N2	117.5 (3)	C13—C12—H12	119.8
C7—N1—Cu1	127.0 (3)	C11—C12—H12	119.8
N2—N1—Cu1	114.7 (2)	C12—C13—C14	120.3 (4)
N1—N2—S1	108.2 (2)	C12—C13—H13	119.9
N1—N2—Cu1ⁱ	122.8 (2)	C14—C13—H13	119.9
S1—N2—Cu1ⁱ	105.85 (17)	C15—C14—C13	119.9 (4)
O1—C1—C2	117.5 (4)	C15—C14—H14	120.0
O1—C1—C6	125.2 (4)	C13—C14—H14	120.0
C2—C1—C6	117.3 (4)	C14—C15—C10	119.3 (4)
C3—C2—C1	122.9 (4)	C14—C15—H15	120.4
C3—C2—H2	118.5	C10—C15—H15	120.4
C1—C2—H2	118.5	S2—C16—H16A	109.5
C2—C3—C4	119.0 (4)	S2—C16—H16B	109.5
C2—C3—H3	120.5	H16A—C16—H16B	109.5
C4—C3—H3	120.5	S2—C16—H16C	109.5
C5—C4—C3	120.7 (4)	H16A—C16—H16C	109.5
C5—C4—Br1	119.9 (3)	H16B—C16—H16C	109.5
C3—C4—Br1	119.3 (3)	S2—C17—H17A	109.5
C4—C5—C6	121.5 (4)	S2—C17—H17B	109.5
C4—C5—H5	119.2	H17A—C17—H17B	109.5
C6—C5—H5	119.2	S2—C17—H17C	109.5
C5—C6—C1	118.4 (4)	H17A—C17—H17C	109.5
C5—C6—C7	119.0 (4)	H17B—C17—H17C	109.5

N1—Cu1—O1—C1	40.0 (3)	C3—C4—C5—C6	−1.3 (7)
O4—Cu1—O1—C1	−152.5 (3)	Br1—C4—C5—C6	−178.1 (3)
N2ⁱ—Cu1—O1—C1	−58.2 (5)	C4—C5—C6—C1	−1.1 (6)
C17—S2—O4—Cu1	−58.7 (3)	C4—C5—C6—C7	−177.5 (4)
C16—S2—O4—Cu1	−161.2 (2)	O1—C1—C6—C5	−177.2 (4)
O1—Cu1—O4—S2	−23.1 (2)	C2—C1—C6—C5	3.2 (6)
N1—Cu1—O4—S2	70.5 (7)	O1—C1—C6—C7	−0.9 (6)
N2ⁱ—Cu1—O4—S2	−176.4 (2)	C2—C1—C6—C7	179.6 (4)
O1—Cu1—N1—C7	−34.4 (4)	N2—N1—C7—C6	−174.7 (3)
O4—Cu1—N1—C7	−128.1 (6)	Cu1—N1—C7—C6	15.4 (5)
N2ⁱ—Cu1—N1—C7	119.1 (3)	N2—N1—C7—C8	5.6 (6)
O1—Cu1—N1—N2	155.5 (3)	Cu1—N1—C7—C8	−164.3 (4)
O4—Cu1—N1—N2	61.8 (7)	C5—C6—C7—N1	−174.6 (4)
N2ⁱ—Cu1—N1—N2	−51.0 (3)	C1—C6—C7—N1	9.1 (6)
C7—N1—N2—S1	132.6 (3)	C5—C6—C7—C8	5.1 (6)
Cu1—N1—N2—S1	−56.4 (3)	C1—C6—C7—C8	−171.2 (4)
C7—N1—N2—Cu1ⁱ	−103.8 (4)	O3—S1—C10—C11	−163.2 (3)
Cu1—N1—N2—Cu1ⁱ	67.3 (3)	O2—S1—C10—C11	−35.1 (4)
O3—S1—N2—N1	166.0 (2)	N2—S1—C10—C11	84.4 (4)
O2—S1—N2—N1	35.8 (3)	O3—S1—C10—C15	16.4 (4)
C10—S1—N2—N1	−79.7 (3)	O2—S1—C10—C15	144.5 (3)
O3—S1—N2—Cu1ⁱ	32.7 (2)	N2—S1—C10—C15	−96.0 (3)
O2—S1—N2—Cu1ⁱ	−97.6 (2)	C15—C10—C11—C12	−0.7 (6)
C10—S1—N2—Cu1ⁱ	146.95 (18)	S1—C10—C11—C12	178.8 (3)
Cu1—O1—C1—C2	148.7 (3)	C10—C11—C12—C13	−0.9 (7)
Cu1—O1—C1—C6	−30.8 (5)	C11—C12—C13—C14	2.1 (7)
O1—C1—C2—C3	177.1 (4)	C12—C13—C14—C15	−1.7 (7)
C6—C1—C2—C3	−3.3 (6)	C13—C14—C15—C10	0.1 (7)
C1—C2—C3—C4	1.1 (7)	C11—C10—C15—C14	1.1 (6)
C2—C3—C4—C5	1.3 (7)	S1—C10—C15—C14	−178.5 (3)
C2—C3—C4—Br1	178.2 (3)

Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₅H₁₁BrN₂O₃S)₂(C₂H₆OS)₂]
M_r	1017.77
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	8.0831 (1), 10.4972 (2), 12.9481 (2)
α, β, γ (°)	68.157 (1), 74.928 (1), 70.691 (1)
V (Å³)	950.56 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	3.49
Crystal size (mm)	0.40 × 0.31 × 0.20

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.335, 0.542
No. of measured, independent and observed [I > 2σ(I)] reflections	12330, 4318, 3788
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.151, 1.21
No. of reflections	4318
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.75, −0.89

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected bond lengths (Å) top

Cu1—O1	1.894 (3)	Cu1—N1	1.967 (3)
Cu1—O4	1.986 (3)	Cu1—N2ⁱ	2.026 (3)

Symmetry code: (i) −x+2, −y+1, −z.

Acknowledgements

The authors thank the University of Canterbury, New Zealand, for the diffraction measurements, and the Science Fund (12–02-03–2031) and the Fundamental Research Grant Scheme (FP064/2006 A) for supporting this study.

References

Ali, H. M., Laila, M., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1617–o1618. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 (Version 2.0-2) and SAINT (Version 7.12A). Bruker AXS Inc., Madison, Wisconsin, USA. 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. (2008). publCIF. In preparation. Google Scholar

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