Weak antiferromagnetic inter­actions in hydro­nium diaqua-1[kappa]O,2[kappa]O-trichloro-1[kappa]Cl,2[kappa]²Cl-[mu]-dimethyl­glycinato-1[kappa]O:2[kappa]²O',N-dimethyl­glycinato-1[kappa]²N,O-dicuprate(II)

The crystal structure of the title compound, (H₃O)[Cu₂(C₄H₈NO₂)₂Cl₃(H₂O)₂], contains two Cu^II ions bridged by the carboxyl­ate group of a dimethyl­glycinate ion in an anti-anti configuration. The Cu^II atoms both have an approximately square-pyramidal conformation geometry and are 5.977 (2) Å apart. The two dimethyl­glycinate ligands have similar conformations, although they play different roles in the structure. A weak antiferromagnetic inter­action between the two copper ions could be inferred from the magnetic susceptibility measurements.

S1. Comment

The establishment of a relationship between the magnetic and structural properties, leading to a better understanding of the fundamental factors governing magnetic properties, has been the aim of a lot of recent scientific work (Khan, 1993). Such knowledge would allow the design and production of new molecular-based magnets, and the comprehension of the structure and function of the paramagnetic active sites in metalloproteins. Metalloproteins justify the great interest in metal carboxylate complexes, since in this systems the metal ions are chelated by carboxylate groups supplied by amino acid chains. Carboxylate is a versatile anion that can display several types of bridging conformations, such as monoatomic or triatomic syn–syn, syn–anti and anti–anti. A soft correlation has been found between the magnetic interaction of the metallic ions with the carboxylate conformation. The triatomic syn–syn conformation usually mediates strong interactions, medium/weak interactions are found in the syn–anti conformation, and the anti–anti conformation favours very weak magnetic exchange interactions. The crystal structure of the title compound, (I), contains two Cu^II ions with different environments bridged by the carboxylate group of a dimethylglycinate ion in an anti–anti configuration (Fig. 1). According to the procedure described by Addison et al. (1984), the shapes of the polyhedra can be considered as square-based pyramidal since the τ values [τ = (θ1-θ2)/60°, where θ1 and θ2 are the largest angles in the coordination sphere) are 0.30 for atom Cu1 and 0.08 for atom Cu2, respectively. (τ is 1 for trigonal-bypyramidal D_3h and 0 for square-based-pyramidal C_4v geometries, respectively.)

The four short bonds occupy the basal positions, and they are of the same type for both Cu1 and Cu2, viz. a carboxylate O atom, a water O atom, an N atom and a Cl atom. As seen in Fig. 1, atom Cu1 is coordinated by a Cl atom in the apical position, with a bond distance of 2.5986 (8) Å. Atom Cu2 has a carboxylate O atom in that position, with a distance of 2.272 (2) Å. As usual, both copper ions deviate from their mean basal plane towards the apical atom [0.2511 (11) Å for Cu1 and 0.2250 (12) Å for Cu2].

The mean basal planes of the pyramids make an angle of 82.24 (5)°. The atoms in the pyramid bases are not equally spaced. The O2—Cu1—O5 angle is 90.19 (9)° and O5—Cu1—Cl2 is 90.10 (8)°, but the Cl2—Cu1—N1 angle is 96.19 (7)° and N1—Cu1—O2 is 82.46 (8)°, and a similar situation is found around atom Cu2. The smaller angle, N1—Cu1—O2, is certainly a result of the incapacity of the organic moiety to stretch further. The distances in the basal plane range between 1.972 (2) and 2.2367 (8) Å for atom Cu1, and 1.9636 (19) and 2.2131 (8) Å for atom Cu2 (Table 1). The two Cu atoms are separated by almost 6 Å. The dimethylglycine molecules crystallize in their ionic form with a total charge of −1. The carboxylate groups are deprotonated, and the C—O distances [1.240 (3)–1.279 (3) Å] are slightly elongated because of their metal coordination role. One of the dimethylglycine moieties bridges the two copper ions, while the other just coordinates atom Cu2. In spite of having distinct functions in this complex, the conformations of the substituted amino acids are similar, both carboxylate groups being rotated 18° around C—C. Usually, the carboxylate groups of bridging dimethylglycine molecules are rotated less than in those in the N,O-coordination mode (Ramos Silva et al., 2005). The molecular skeletons deviate from planarity, as indicated by the C3—N1—C2—C1 [−159.1 (2)°] and C7—N2—C6—C5 [159.4 (2)°] torsion angles. Both chelate rings are significantly non-planar, as illustrated by the N1—C2—C1—O2 [18.0 (3)] and N2—C6—C5—O3 [−17.5 (3)°] torsion angles. In a related compound, aquabis(N,N-dimethylglycinato)copper dihydrate (Cameron et al., 1973), where amino acid ions chelate each metallic cation in an N,O-chelating mode, and the apical position is taken by an water O atom, the torsion angles (of the chelate rings) are approximately 18 and 30°. Such a conformation goes against that expected from the results of a density functional study in the gas phase for Cu⁺– and Cu²⁺–glycine bonding (Bertran et al., 1999), using the hybrid three-parameter B3LYP approach. These calculations showed that for Cu⁺ the most stable coordination is N,O-bidentate, with the cation interacting with the N and carbonyl O atoms. For Cu²⁺, the preferred coordination is O,O-bidentate, with the metal interacting with the CO₂⁻ group of the zwitterionic species.

A hydronium cation compensates the complex negative charge and links three neighbouring complexes via hydrogen bonds (Table 2). The coordination water molecules also share their H atoms with the carboxylate O atoms and atom Cl1, exhausting their potential as donors. Fig. 2 shows the projection of the molecular packing down the b axis and the ring patterns formed by the hydronium hydrogen bonds. Perpendicular to the b axis, three water H atoms shared with other complexes delineate infinite chains. The remaining H atom participates in rings composed of symmetry-inverted molecules, completing a two-dimensional hydorgen-bond network parallel to the (100) plane. The temperature dependence of the magnetic susceptibility of the title compound was measured using a SQUID magnetometer. An external magnetic field of 100 Oe was applied on a powder sample weighing 0.0277 g. Only a small antiferromagnetic interaction between the sample copper ions could be measured. Indeed, as previous work has pointed out, an anti–anti bridging is not favourable for an antiferromagnetic interaction, and even weak ferromagnetic coupling has been found (Suarez-Varela et al., 1995).

S2. Experimental

Dimethylglycine (5 mmol) was added to hydrated copper chloride (2.5 mmol) in aqueous solution. After a few months at room temperature, small single crystals had grown and their structure was determined using X-ray analysis (Ramos Silva et al., 2005). After a few weeks, all those crystals had spontaneously dissolved in the solution, and a few weeks later new crystals of the title compound formed.

S3. Refinement

The amino acid H atoms were placed at calculated positions and refined as riding on their parent C atoms, with C—H distances of 0.96 and 0.97 Å and with U_iso(H) values of 1.2 or 1.5 times U_eq(C). Water and hydronium H atoms were located in a difference Fourier map and their positions were refined; U_iso(H) values were set at 1.2 or 1.5 times U_eq(O), respectively. Examination of the crystal structure with PLATON (Spek, 2003) showed that there are no solvent-accessible voids.

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The packing of the molecules, projected along b. Hydrogen bonds are drawn as dashed lines.

hydronium diaqua-1κO,2κO-trichloro-1κCl;2κ²Cl-µ-dimethylglycinato-1κO:2κ²O',N- dimethylglycinato-1κ²N,O-dicuprate(II)

Crystal data

(H3O)[Cu2Cl3(C4H8NO2)2(H2O)2]	F(000) = 1000
Mr = 492.71	Dx = 1.768 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.6775 (10) Å	Cell parameters from 25 reflections
b = 6.2641 (4) Å	θ = 11.8–19.8°
c = 22.811 (2) Å	µ = 2.76 mm^−1
β = 124.292 (6)°	T = 293 K
V = 1850.8 (3) Å^3	Prism, blue
Z = 4	0.44 × 0.29 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	3204 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 27.5°, θmin = 3.2°
Profile data from ω–2θ scans	h = 0→20
Absorption correction: ψ scan (North et al., 1968)	k = −8→0
Tmin = 0.485, Tmax = 0.718	l = −29→24
4372 measured reflections	3 standard reflections every 180 min
4220 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0526P)^2 + 0.8128P] where P = (Fo^2 + 2Fc^2)/3
4220 reflections	(Δ/σ)max < 0.001
224 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.56 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.79180 (3)	0.59563 (5)	0.935126 (17)	0.02654 (10)
Cu2	0.77286 (2)	0.07686 (5)	0.708127 (17)	0.02666 (10)
Cl1	0.89865 (6)	0.27087 (11)	1.01316 (4)	0.03647 (17)
Cl2	0.71235 (7)	0.74033 (13)	0.98182 (5)	0.04314 (19)
Cl3	0.64579 (6)	−0.11121 (12)	0.69816 (5)	0.04075 (18)
O1	0.81926 (15)	0.3447 (4)	0.78790 (10)	0.0353 (5)
O2	0.83029 (15)	0.5732 (3)	0.86510 (10)	0.0319 (4)
O3	0.88044 (14)	0.1815 (3)	0.69637 (10)	0.0298 (4)
O4	0.92472 (16)	0.4729 (3)	0.66495 (12)	0.0379 (5)
O5	0.91354 (19)	0.7772 (4)	0.99674 (13)	0.0408 (5)
H51	0.903 (3)	0.916 (7)	0.997 (2)	0.049*
H52	0.958 (3)	0.773 (6)	0.991 (2)	0.049*
O6	0.8767 (2)	−0.1286 (5)	0.77868 (16)	0.0520 (7)
H61	0.869 (4)	−0.169 (8)	0.800 (3)	0.062*
H62	0.935 (4)	−0.110 (7)	0.793 (2)	0.062*
O7	1.0356 (2)	0.3955 (4)	0.85651 (14)	0.0486 (6)
H71	0.953 (4)	0.388 (7)	0.827 (2)	0.073*
H72	1.057 (3)	0.496 (8)	0.830 (2)	0.073*
H73	1.063 (3)	0.486 (8)	0.902 (3)	0.073*
N1	0.67234 (17)	0.4130 (4)	0.86306 (11)	0.0259 (5)
N2	0.68306 (17)	0.2782 (4)	0.62596 (12)	0.0277 (5)
C1	0.79320 (19)	0.4090 (5)	0.82703 (13)	0.0267 (5)
C2	0.7150 (2)	0.2827 (5)	0.83157 (15)	0.0312 (6)
H2A	0.6595	0.2370	0.7844	0.037*
H2B	0.7476	0.1563	0.8603	0.037*
C3	0.6279 (2)	0.2719 (5)	0.89159 (15)	0.0344 (6)
H3A	0.5738	0.1867	0.8539	0.052*
H3B	0.6001	0.3575	0.9120	0.052*
H3C	0.6809	0.1802	0.9273	0.052*
C4	0.5913 (2)	0.5563 (6)	0.80885 (16)	0.0418 (7)
H4A	0.5341	0.4728	0.7728	0.063*
H4B	0.6186	0.6397	0.7878	0.063*
H4C	0.5683	0.6496	0.8307	0.063*
C5	0.8607 (2)	0.3649 (5)	0.66682 (13)	0.0272 (6)
C6	0.7538 (2)	0.4503 (5)	0.63561 (15)	0.0310 (6)
H6A	0.7559	0.5585	0.6668	0.037*
H6B	0.7285	0.5165	0.5902	0.037*
C7	0.5917 (2)	0.3666 (6)	0.62082 (18)	0.0413 (7)
H7A	0.6133	0.4397	0.6641	0.062*
H7B	0.5456	0.2526	0.6132	0.062*
H7C	0.5570	0.4650	0.5818	0.062*
C8	0.6480 (3)	0.1583 (7)	0.55975 (17)	0.0526 (9)
H8A	0.6092	0.2516	0.5196	0.079*
H8B	0.6052	0.0410	0.5551	0.079*
H8C	0.7070	0.1048	0.5617	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.02987 (18)	0.02634 (18)	0.02809 (17)	−0.00363 (14)	0.01915 (14)	−0.00560 (13)
Cu2	0.02481 (17)	0.02666 (17)	0.03229 (18)	−0.00024 (13)	0.01839 (14)	0.00093 (14)
Cl1	0.0353 (4)	0.0273 (3)	0.0389 (4)	0.0012 (3)	0.0162 (3)	−0.0020 (3)
Cl2	0.0590 (5)	0.0380 (4)	0.0542 (5)	−0.0021 (4)	0.0451 (4)	−0.0091 (3)
Cl3	0.0356 (4)	0.0365 (4)	0.0576 (5)	−0.0080 (3)	0.0307 (4)	−0.0022 (3)
O1	0.0334 (10)	0.0487 (12)	0.0334 (10)	−0.0082 (10)	0.0245 (9)	−0.0109 (10)
O2	0.0323 (10)	0.0375 (11)	0.0324 (10)	−0.0097 (9)	0.0222 (9)	−0.0085 (9)
O3	0.0285 (10)	0.0332 (10)	0.0352 (10)	0.0032 (8)	0.0224 (9)	0.0038 (9)
O4	0.0322 (11)	0.0393 (12)	0.0482 (12)	−0.0049 (9)	0.0263 (10)	0.0012 (10)
N1	0.0251 (10)	0.0324 (12)	0.0236 (10)	−0.0022 (9)	0.0157 (9)	−0.0008 (9)
N2	0.0242 (11)	0.0356 (12)	0.0243 (11)	−0.0003 (10)	0.0143 (9)	−0.0034 (10)
C1	0.0199 (12)	0.0372 (15)	0.0212 (11)	0.0010 (11)	0.0105 (10)	0.0003 (11)
C2	0.0327 (14)	0.0370 (15)	0.0313 (14)	−0.0105 (12)	0.0226 (12)	−0.0110 (12)
C3	0.0325 (15)	0.0439 (17)	0.0331 (15)	−0.0074 (13)	0.0224 (13)	0.0016 (13)
C4	0.0318 (15)	0.057 (2)	0.0359 (15)	0.0063 (15)	0.0184 (13)	0.0144 (15)
C5	0.0296 (13)	0.0328 (14)	0.0218 (12)	0.0011 (11)	0.0161 (11)	−0.0020 (11)
C6	0.0319 (14)	0.0325 (14)	0.0314 (13)	0.0033 (12)	0.0195 (12)	0.0079 (12)
C7	0.0292 (15)	0.0477 (18)	0.0460 (18)	0.0066 (14)	0.0207 (14)	0.0048 (15)
C8	0.051 (2)	0.070 (2)	0.0312 (16)	−0.0045 (19)	0.0194 (15)	−0.0156 (17)
O7	0.0471 (14)	0.0521 (15)	0.0518 (14)	−0.0093 (12)	0.0309 (12)	−0.0062 (12)
O6	0.0320 (12)	0.0500 (15)	0.0691 (18)	0.0056 (11)	0.0254 (13)	0.0270 (13)
O5	0.0409 (13)	0.0318 (11)	0.0527 (14)	−0.0095 (10)	0.0282 (11)	−0.0147 (10)

Geometric parameters (Å, º)

Cu1—O5	1.972 (2)	C3—H3A	0.9600
Cu1—O2	2.0055 (19)	C3—H3B	0.9600
Cu1—N1	2.012 (2)	C3—H3C	0.9600
Cu1—Cl2	2.2367 (8)	C4—H4A	0.9600
Cu1—Cl1	2.5986 (8)	C4—H4B	0.9600
Cu2—O3	1.9636 (19)	C4—H4C	0.9600
Cu2—O6	1.986 (3)	C5—C6	1.503 (4)
Cu2—N2	2.028 (2)	C6—H6A	0.9700
Cu2—Cl3	2.2131 (8)	C6—H6B	0.9700
Cu2—O1	2.272 (2)	C7—H7A	0.9600
O1—C1	1.240 (3)	C7—H7B	0.9600
O2—C1	1.257 (3)	C7—H7C	0.9600
O3—C5	1.279 (3)	C8—H8A	0.9600
O4—C5	1.231 (3)	C8—H8B	0.9600
N1—C2	1.473 (3)	C8—H8C	0.9600
N1—C4	1.476 (4)	O7—H71	1.07 (5)
N1—C3	1.484 (3)	O7—H72	1.05 (5)
N2—C6	1.471 (4)	O7—H73	1.04 (5)
N2—C7	1.477 (4)	O6—H61	0.62 (5)
N2—C8	1.487 (4)	O6—H62	0.78 (5)
C1—C2	1.512 (4)	O5—H51	0.89 (4)
C2—H2A	0.9700	O5—H52	0.78 (4)
C2—H2B	0.9700
O5—Cu1—O2	90.19 (9)	H2A—C2—H2B	108.1
O5—Cu1—N1	172.60 (10)	N1—C3—H3A	109.5
O2—Cu1—N1	82.46 (8)	N1—C3—H3B	109.5
O5—Cu1—Cl2	90.10 (8)	H3A—C3—H3B	109.5
O2—Cu1—Cl2	154.95 (7)	N1—C3—H3C	109.5
N1—Cu1—Cl2	96.19 (7)	H3A—C3—H3C	109.5
O5—Cu1—Cl1	88.39 (8)	H3B—C3—H3C	109.5
O2—Cu1—Cl1	97.10 (6)	N1—C4—H4A	109.5
N1—Cu1—Cl1	93.36 (7)	N1—C4—H4B	109.5
Cl2—Cu1—Cl1	107.94 (3)	H4A—C4—H4B	109.5
O3—Cu2—O6	87.24 (10)	N1—C4—H4C	109.5
O3—Cu2—N2	82.45 (9)	H4A—C4—H4C	109.5
O6—Cu2—N2	167.74 (11)	H4B—C4—H4C	109.5
O3—Cu2—Cl3	163.01 (7)	O4—C5—O3	123.5 (3)
O6—Cu2—Cl3	91.02 (8)	O4—C5—C6	120.1 (3)
N2—Cu2—Cl3	96.90 (7)	O3—C5—C6	116.3 (2)
O3—Cu2—O1	87.18 (8)	N2—C6—C5	110.8 (2)
O6—Cu2—O1	94.78 (12)	N2—C6—H6A	109.5
N2—Cu2—O1	91.33 (9)	C5—C6—H6A	109.5
Cl3—Cu2—O1	109.81 (5)	N2—C6—H6B	109.5
C1—O1—Cu2	136.87 (19)	C5—C6—H6B	109.5
C1—O2—Cu1	112.19 (17)	H6A—C6—H6B	108.1
C5—O3—Cu2	113.62 (17)	N2—C7—H7A	109.5
C2—N1—C4	110.0 (2)	N2—C7—H7B	109.5
C2—N1—C3	109.8 (2)	H7A—C7—H7B	109.5
C4—N1—C3	109.5 (2)	N2—C7—H7C	109.5
C2—N1—Cu1	104.15 (16)	H7A—C7—H7C	109.5
C4—N1—Cu1	107.73 (19)	H7B—C7—H7C	109.5
C3—N1—Cu1	115.55 (17)	N2—C8—H8A	109.5
C6—N2—C7	110.6 (2)	N2—C8—H8B	109.5
C6—N2—C8	109.8 (2)	H8A—C8—H8B	109.5
C7—N2—C8	108.8 (2)	N2—C8—H8C	109.5
C6—N2—Cu2	104.19 (16)	H8A—C8—H8C	109.5
C7—N2—Cu2	116.34 (18)	H8B—C8—H8C	109.5
C8—N2—Cu2	106.9 (2)	H71—O7—H72	110 (3)
O1—C1—O2	123.5 (3)	H71—O7—H73	109 (3)
O1—C1—C2	119.2 (3)	H72—O7—H73	100 (3)
O2—C1—C2	117.3 (2)	Cu2—O6—H61	118 (5)
N1—C2—C1	110.6 (2)	Cu2—O6—H62	119 (3)
N1—C2—H2A	109.5	H61—O6—H62	115 (6)
C1—C2—H2A	109.5	Cu1—O5—H51	118 (3)
N1—C2—H2B	109.5	Cu1—O5—H52	118 (3)
C1—C2—H2B	109.5	H51—O5—H52	103 (4)
O3—Cu2—O1—C1	−178.6 (3)	O3—Cu2—N2—C7	−153.0 (2)
O6—Cu2—O1—C1	−91.6 (3)	O6—Cu2—N2—C7	174.1 (5)
N2—Cu2—O1—C1	99.1 (3)	Cl3—Cu2—N2—C7	44.2 (2)
Cl3—Cu2—O1—C1	1.2 (3)	O1—Cu2—N2—C7	−66.0 (2)
O5—Cu1—O2—C1	156.33 (19)	O3—Cu2—N2—C8	85.3 (2)
N1—Cu1—O2—C1	−24.54 (19)	O6—Cu2—N2—C8	52.3 (6)
Cl2—Cu1—O2—C1	−113.0 (2)	Cl3—Cu2—N2—C8	−77.6 (2)
Cl1—Cu1—O2—C1	67.93 (18)	O1—Cu2—N2—C8	172.3 (2)
O6—Cu2—O3—C5	−162.6 (2)	Cu2—O1—C1—O2	−176.76 (19)
N2—Cu2—O3—C5	24.09 (18)	Cu2—O1—C1—C2	5.0 (4)
Cl3—Cu2—O3—C5	113.0 (2)	Cu1—O2—C1—O1	−168.6 (2)
O1—Cu2—O3—C5	−67.63 (18)	Cu1—O2—C1—C2	9.8 (3)
O2—Cu1—N1—C2	31.70 (17)	C4—N1—C2—C1	80.4 (3)
Cl2—Cu1—N1—C2	−173.50 (16)	C3—N1—C2—C1	−159.1 (2)
Cl1—Cu1—N1—C2	−65.03 (16)	Cu1—N1—C2—C1	−34.8 (3)
O2—Cu1—N1—C4	−85.07 (18)	O1—C1—C2—N1	−163.6 (2)
Cl2—Cu1—N1—C4	69.73 (17)	O2—C1—C2—N1	18.0 (3)
Cl1—Cu1—N1—C4	178.20 (17)	Cu2—O3—C5—O4	167.9 (2)
O2—Cu1—N1—C3	152.2 (2)	Cu2—O3—C5—C6	−9.9 (3)
Cl2—Cu1—N1—C3	−53.0 (2)	C7—N2—C6—C5	159.4 (2)
Cl1—Cu1—N1—C3	55.4 (2)	C8—N2—C6—C5	−80.6 (3)
O3—Cu2—N2—C6	−30.90 (17)	Cu2—N2—C6—C5	33.6 (2)
O6—Cu2—N2—C6	−63.9 (6)	O4—C5—C6—N2	164.6 (2)
Cl3—Cu2—N2—C6	166.21 (16)	O3—C5—C6—N2	−17.5 (3)
O1—Cu2—N2—C6	56.08 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···Cl1^i	0.89 (4)	2.26 (4)	3.139 (2)	172 (4)
O5—H52···Cl1^ii	0.78 (4)	2.31 (4)	3.092 (3)	172 (4)
O6—H61···O2^iii	0.62 (5)	2.49 (5)	3.086 (3)	164 (6)
O6—H62···O4^iv	0.78 (5)	1.92 (5)	2.690 (3)	172 (5)
O7—H71···O1	1.07 (5)	1.77 (5)	2.841 (3)	172 (4)
O7—H72···O3^v	1.05 (5)	1.83 (5)	2.861 (3)	168 (4)
O7—H73···Cl1^ii	1.04 (5)	2.26 (5)	3.289 (3)	169 (4)

Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, −z+2; (iii) x, y−1, z; (iv) −x+2, y−1/2, −z+3/2; (v) −x+2, y+1/2, −z+3/2.