Diaqua­bis­(perchlorato)(1,10-phenanthroline)copper(II)

In the title compound, [Cu(ClO₄)₂(C₁₂H₈N₂)(H₂O)₂], the Cu^II atom is coordinated in a square-planar fashion by the two N atoms of a chelating 1,10-phenanthroline ligand and by two water mol­ecules trans to the N atoms. The coordination sphere of the metal atom is augmented by O atoms of two weakly bonded perchlorate anions, thus yielding a strongly distorted CuN₂O₄ octa­hedral environment. The crystal packing is stabilized by O—H...O hydrogen bonds between the water mol­ecules and the perchlorate anions. In addition, the organic mol­ecules are associated by π–π stacking inter­actions between symmetry-equivalent anti­parallel non-nitro­gen aromatic rings, with inter­planar distances of 3.543 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.024
• wR factor = 0.074
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop           1

Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    --  O1      ..       5.48 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    --  O2      ..       5.78 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    --  O3      ..       9.34 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cl2
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          6
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600        471

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

In recent years, there has been an active and concerted attention in developing metal-organic coordination materials owing to their potentially useful magnetic, electric, photochemical and catalytic properties (Kubo, 1976; Kobel & Hanack, 1986; Pierpont & Jung, 1994; Huskins & Robson, 1990). Here, the title compound, [Cu(H₂O)₂(C₁₂H₈N₂)](ClO₄)₂, is presented, which has been obtained in continuation of our studies of new coordination compounds (Kaabi, et al., 2010).

In the atomic arrangement of the title material, the Cu ion is surrounded by one 1,10-phenanthroline ligand, two ClO₄^- anions and two water molecules. The Cu^II atom is coordinated in a square-planar fashion by two nitrogen atoms of a chelating o-phenanthroline ligand and two water molecules trans to the nitrogen atoms with Cu—N1 and Cu—N2 distances of 1.9953 (12) and 1.9764 (12) Å, and Cu—O1 and Cu—O2 distances of 1.9784 (10) and 1.9600 (11) Å, respectively. The coordination sphere around the metal is augmented by oxygen atoms of two weakly bound perchlorate anions, thus yielding a strongly distorted octahedral environment for the copper(II) ion (Fig. 1). The two Cu—O distances to the perchlorate anions, 2.3805 (11) and 2.5508 (11) Å, are much longer than the Cu—O(water) distances (Table 1), and especially the longer of these two distances should be regarded as a very weak interaction rather than an actual metal-oxygen bond.

The complexes are interconnected by a set of O—H···O hydrogen bonds between the water molecules and the perchlorate anions (Table 2), leading to the formation of a three dimensional network (Fig. 2). As expected, the ClO₄^- anion has a characteristic tetrahedral geometry where the Cl—O bond lengths and O—Cl—O angles are slightly different from one another and vary with the coordination of the individual O atoms, such as hydrogen bonds or metal coordination. In the title compound, the Cl—O bond lengths vary between 1.4272 (13) and 1.4728 (11) Å and 1.4230 (14) and 1.4490 (11) Å for the two ClO₄^- anions. The O—Cl—O angles range from 107.95 (7) to 111.67 (10)° for the first anion and from 108.62 (7) to 110.48 (11)° for the second anion.

Intermolecular π–π stacking interactions between neighboring non-nitrogen aromatic rings of 1,10-phenanthroline are also observed, with a face-to-face distance of 3.543 (2) Å (Fig. 3), less than 3.8 Å, the maximum value regarded as relevant for π–π interactions (Janiak, 2000).

Related literature

For common applications of metal-organic coordination compounds, see: Kubo (1976); Kobel & Hanack (1986); Pierpont & Jung (1994); Huskins & Robson (1990). For a related structure, see: Kaabi et al. (2010). For π-π interactions, see: Janiak (2000).

S2. Experimental

An aqueous solution of Cu(ClO₄)₂ (1 mmol, 0.263 g) was added dropwise to a solution of 1,10-phenanthroline (1 mmol, 0.180 g) in ethanol. The resultant mixture was evaporated at room temperature. Crystals of the title compound, which remained stable under normal conditions of temperature and humidity, were isolated after several days and subjected to X-ray diffraction analysis (yield 63%).

S3. Refinement

C—H hydrogen atoms were placed in calculated positions with C—H distances in the range 0.93–0.97 Å. The water hydrogen atom postitions were refined with O—H distance restraints of 0.84 (2) Å. The U_iso(H) values of all H atoms were constrained to 1.2 or 1.5× U_eq of the respective parent atom.

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. A view of the asymmetric unit of the title compound, showing 50% probability displacement ellipsoids, arbitrary spheres for the H atoms, and the atom numbering scheme.
	Fig. 2. The packing of [Cu(H2O)2(C12H8N2)](ClO4)2, viewed down the b axis. Hydrogen bonds are denoted by dotted lines.
	Fig. 3. π-π stacking interactions in [Cu(H2O)2(C12H8N2)](ClO4)2.

Diaquabis(perchlorato)(1,10-phenanthroline)copper(II)

Crystal data

[Cu(ClO4)2(C12H8N2)(H2O)2]	Z = 2
Mr = 478.68	F(000) = 482
Triclinic, P1	Dx = 1.942 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7882 (10) Å	Cell parameters from 6809 reflections
b = 10.4226 (14) Å	θ = 2.5–31.1°
c = 10.8065 (14) Å	µ = 1.72 mm^−1
α = 76.567 (1)°	T = 100 K
β = 75.227 (2)°	Rod, blue
γ = 79.801 (2)°	0.45 × 0.25 × 0.21 mm
V = 818.50 (19) Å^3

Data collection

Bruker APEXII CCD diffractometer	4872 independent reflections
Radiation source: fine-focus sealed tube	4647 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scans	θmax = 31.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.587, Tmax = 0.746	k = −14→14
17211 measured reflections	l = −15→15

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0396P)^2 + 0.4561P] where P = (Fo^2 + 2Fc^2)/3
4872 reflections	(Δ/σ)max = 0.003
256 parameters	Δρmax = 0.48 e Å^−3
4 restraints	Δρmin = −0.53 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
C1	0.48090 (19)	1.03799 (14)	0.78959 (15)	0.0155 (2)
H1	0.4156	1.0302	0.8776	0.019*
C2	0.4523 (2)	1.15657 (14)	0.70023 (16)	0.0186 (3)
H2	0.3690	1.2282	0.7281	0.022*
C3	0.5448 (2)	1.16911 (14)	0.57240 (16)	0.0189 (3)
H3	0.5258	1.2493	0.5116	0.023*
C4	0.66839 (19)	1.06189 (14)	0.53204 (14)	0.0151 (2)
C5	0.69072 (18)	0.94807 (13)	0.62763 (13)	0.0122 (2)
C6	0.81967 (18)	0.83761 (13)	0.59601 (13)	0.0129 (2)
C7	0.91968 (19)	0.84133 (15)	0.46757 (14)	0.0160 (3)
C8	1.0478 (2)	0.72975 (16)	0.44474 (15)	0.0191 (3)
H8	1.1164	0.7254	0.3591	0.023*
C9	1.0719 (2)	0.62824 (16)	0.54732 (16)	0.0200 (3)
H9	1.1602	0.5543	0.5335	0.024*
C10	0.96612 (19)	0.63344 (15)	0.67308 (15)	0.0174 (3)
H10	0.9845	0.5623	0.7433	0.021*
C11	0.7716 (2)	1.06372 (16)	0.40131 (15)	0.0188 (3)
H11	0.7564	1.1404	0.3356	0.023*
C12	0.8908 (2)	0.95768 (16)	0.36975 (15)	0.0192 (3)
H12	0.9557	0.9605	0.2821	0.023*
Cl1	0.49764 (5)	0.52161 (3)	0.72929 (3)	0.01545 (7)
Cl2	0.99352 (4)	0.77378 (3)	1.00887 (3)	0.01565 (7)
Cu1	0.65728 (2)	0.758637 (15)	0.858913 (15)	0.01130 (6)
N1	0.84121 (16)	0.73496 (12)	0.69669 (12)	0.0131 (2)
N2	0.59768 (15)	0.93583 (11)	0.75385 (12)	0.0124 (2)
O1	0.45249 (14)	0.78997 (10)	1.00501 (10)	0.01413 (19)
H1A	0.446 (3)	0.7260 (18)	1.0657 (18)	0.021*
H1B	0.357 (2)	0.808 (2)	0.986 (2)	0.021*
O2	0.70251 (15)	0.57653 (11)	0.95518 (11)	0.0177 (2)
H2A	0.689 (3)	0.520 (2)	0.918 (2)	0.027*
H2B	0.786 (3)	0.555 (2)	0.989 (2)	0.027*
O3	0.45492 (15)	0.64314 (11)	0.77965 (12)	0.0194 (2)
O4	0.5846 (2)	0.54920 (15)	0.59434 (12)	0.0395 (4)
O5	0.62326 (14)	0.42954 (10)	0.79995 (11)	0.0176 (2)
O6	0.33842 (17)	0.46231 (12)	0.74967 (14)	0.0276 (3)
O7	1.13473 (15)	0.84737 (12)	0.92507 (12)	0.0240 (2)
O8	1.02607 (18)	0.64014 (13)	0.98634 (18)	0.0372 (4)
O9	0.82443 (14)	0.83601 (12)	0.97691 (13)	0.0219 (2)
O10	0.9878 (2)	0.77359 (19)	1.14159 (13)	0.0417 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0146 (6)	0.0133 (6)	0.0188 (6)	−0.0006 (5)	−0.0038 (5)	−0.0044 (5)
C2	0.0178 (7)	0.0118 (6)	0.0260 (7)	−0.0001 (5)	−0.0062 (5)	−0.0031 (5)
C3	0.0184 (7)	0.0125 (6)	0.0253 (7)	−0.0030 (5)	−0.0088 (5)	0.0021 (5)
C4	0.0162 (6)	0.0150 (6)	0.0155 (6)	−0.0056 (5)	−0.0064 (5)	0.0004 (5)
C5	0.0123 (6)	0.0128 (5)	0.0127 (6)	−0.0030 (4)	−0.0042 (4)	−0.0020 (4)
C6	0.0115 (6)	0.0146 (6)	0.0137 (6)	−0.0030 (4)	−0.0032 (4)	−0.0039 (5)
C7	0.0143 (6)	0.0210 (6)	0.0146 (6)	−0.0059 (5)	−0.0023 (5)	−0.0055 (5)
C8	0.0155 (6)	0.0273 (7)	0.0167 (7)	−0.0045 (5)	0.0004 (5)	−0.0117 (6)
C9	0.0149 (6)	0.0225 (7)	0.0233 (7)	0.0009 (5)	−0.0013 (5)	−0.0117 (6)
C10	0.0138 (6)	0.0165 (6)	0.0212 (7)	0.0015 (5)	−0.0031 (5)	−0.0058 (5)
C11	0.0207 (7)	0.0208 (7)	0.0153 (6)	−0.0085 (5)	−0.0058 (5)	0.0020 (5)
C12	0.0201 (7)	0.0265 (7)	0.0126 (6)	−0.0097 (6)	−0.0029 (5)	−0.0025 (5)
Cl1	0.01850 (16)	0.01185 (14)	0.01345 (15)	0.00302 (11)	−0.00298 (11)	−0.00183 (11)
Cl2	0.01062 (14)	0.01961 (15)	0.01699 (16)	−0.00126 (11)	−0.00489 (11)	−0.00257 (12)
Cu1	0.01059 (9)	0.01082 (8)	0.01119 (9)	0.00001 (6)	−0.00176 (6)	−0.00135 (6)
N1	0.0114 (5)	0.0138 (5)	0.0140 (5)	−0.0007 (4)	−0.0025 (4)	−0.0034 (4)
N2	0.0107 (5)	0.0117 (5)	0.0144 (5)	−0.0011 (4)	−0.0022 (4)	−0.0026 (4)
O1	0.0117 (4)	0.0152 (5)	0.0138 (5)	−0.0007 (4)	−0.0025 (3)	−0.0006 (4)
O2	0.0173 (5)	0.0162 (5)	0.0179 (5)	0.0019 (4)	−0.0068 (4)	0.0002 (4)
O3	0.0171 (5)	0.0128 (5)	0.0294 (6)	0.0025 (4)	−0.0069 (4)	−0.0076 (4)
O4	0.0498 (9)	0.0364 (7)	0.0130 (6)	0.0210 (6)	0.0030 (5)	0.0024 (5)
O5	0.0173 (5)	0.0136 (4)	0.0185 (5)	0.0028 (4)	−0.0046 (4)	0.0009 (4)
O6	0.0281 (6)	0.0185 (5)	0.0433 (8)	−0.0014 (5)	−0.0200 (5)	−0.0080 (5)
O7	0.0150 (5)	0.0291 (6)	0.0238 (6)	−0.0059 (4)	−0.0039 (4)	0.0046 (5)
O8	0.0221 (6)	0.0175 (6)	0.0769 (11)	0.0048 (5)	−0.0222 (7)	−0.0121 (6)
O9	0.0120 (5)	0.0236 (5)	0.0347 (6)	0.0050 (4)	−0.0109 (4)	−0.0142 (5)
O10	0.0322 (7)	0.0777 (12)	0.0163 (6)	−0.0136 (7)	−0.0070 (5)	−0.0046 (7)

Geometric parameters (Å, º)

C1—N2	1.3338 (17)	C11—C12	1.360 (2)
C1—C2	1.403 (2)	C11—H11	0.9500
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.373 (2)	Cl1—O6	1.4272 (13)
C2—H2	0.9500	Cl1—O4	1.4277 (13)
C3—C4	1.413 (2)	Cl1—O3	1.4456 (11)
C3—H3	0.9500	Cl1—O5	1.4728 (11)
C4—C5	1.3978 (19)	Cl2—O10	1.4230 (14)
C4—C11	1.434 (2)	Cl2—O8	1.4369 (13)
C5—N2	1.3600 (18)	Cl2—O7	1.4443 (12)
C5—C6	1.4315 (19)	Cl2—O9	1.4490 (11)
C6—N1	1.3583 (18)	Cu1—O2	1.9600 (11)
C6—C7	1.4033 (19)	Cu1—N2	1.9764 (12)
C7—C8	1.416 (2)	Cu1—O1	1.9784 (10)
C7—C12	1.438 (2)	Cu1—N1	1.9953 (12)
C8—C9	1.369 (2)	Cu1—O9	2.3805 (11)
C8—H8	0.9500	Cu1—O3	2.5508 (11)
C9—C10	1.406 (2)	O1—H1A	0.818 (15)
C9—H9	0.9500	O1—H1B	0.800 (16)
C10—N1	1.3287 (18)	O2—H2A	0.828 (16)
C10—H10	0.9500	O2—H2B	0.796 (16)
N2—C1—C2	121.54 (14)	O6—Cl1—O5	109.27 (7)
N2—C1—H1	119.2	O4—Cl1—O5	107.95 (7)
C2—C1—H1	119.2	O3—Cl1—O5	108.49 (7)
C3—C2—C1	119.98 (14)	O10—Cl2—O8	110.48 (11)
C3—C2—H2	120.0	O10—Cl2—O7	109.54 (9)
C1—C2—H2	120.0	O8—Cl2—O7	109.21 (9)
C2—C3—C4	119.50 (13)	O10—Cl2—O9	109.96 (9)
C2—C3—H3	120.2	O8—Cl2—O9	108.62 (7)
C4—C3—H3	120.2	O7—Cl2—O9	109.00 (7)
C5—C4—C3	116.85 (13)	O2—Cu1—N2	174.66 (5)
C5—C4—C11	118.86 (14)	O2—Cu1—O1	88.24 (5)
C3—C4—C11	124.28 (14)	N2—Cu1—O1	91.93 (5)
N2—C5—C4	123.37 (13)	O2—Cu1—N1	96.05 (5)
N2—C5—C6	116.35 (12)	N2—Cu1—N1	83.24 (5)
C4—C5—C6	120.26 (13)	O1—Cu1—N1	172.57 (5)
N1—C6—C7	123.64 (13)	O2—Cu1—O9	90.50 (5)
N1—C6—C5	116.32 (12)	N2—Cu1—O9	94.84 (5)
C7—C6—C5	120.02 (13)	O1—Cu1—O9	84.57 (4)
C6—C7—C8	116.66 (14)	N1—Cu1—O9	101.41 (5)
C6—C7—C12	118.86 (14)	O2—Cu1—O3	79.80 (4)
C8—C7—C12	124.45 (14)	N2—Cu1—O3	94.87 (4)
C9—C8—C7	119.34 (14)	O1—Cu1—O3	87.45 (4)
C9—C8—H8	120.3	N1—Cu1—O3	87.35 (4)
C7—C8—H8	120.3	O9—Cu1—O3	167.63 (4)
C8—C9—C10	120.01 (14)	C10—N1—C6	118.35 (13)
C8—C9—H9	120.0	C10—N1—Cu1	130.12 (11)
C10—C9—H9	120.0	C6—N1—Cu1	111.33 (9)
N1—C10—C9	121.96 (14)	C1—N2—C5	118.73 (12)
N1—C10—H10	119.0	C1—N2—Cu1	129.24 (10)
C9—C10—H10	119.0	C5—N2—Cu1	112.01 (9)
C12—C11—C4	121.18 (14)	Cu1—O1—H1A	111.7 (15)
C12—C11—H11	119.4	Cu1—O1—H1B	114.7 (16)
C4—C11—H11	119.4	H1A—O1—H1B	108 (2)
C11—C12—C7	120.77 (14)	Cu1—O2—H2A	113.0 (16)
C11—C12—H12	119.6	Cu1—O2—H2B	120.8 (17)
C7—C12—H12	119.6	H2A—O2—H2B	112 (2)
O6—Cl1—O4	111.67 (10)	Cl1—O3—Cu1	128.58 (6)
O6—Cl1—O3	109.72 (7)	Cl2—O9—Cu1	127.20 (7)
O4—Cl1—O3	109.67 (8)
N2—C1—C2—C3	0.4 (2)	O2—Cu1—N1—C6	166.74 (9)
C1—C2—C3—C4	0.0 (2)	N2—Cu1—N1—C6	−7.93 (9)
C2—C3—C4—C5	−0.9 (2)	O9—Cu1—N1—C6	−101.53 (9)
C2—C3—C4—C11	179.75 (14)	O3—Cu1—N1—C6	87.29 (9)
C3—C4—C5—N2	1.5 (2)	C2—C1—N2—C5	0.1 (2)
C11—C4—C5—N2	−179.12 (12)	C2—C1—N2—Cu1	−178.36 (11)
C3—C4—C5—C6	−176.98 (12)	C4—C5—N2—C1	−1.1 (2)
C11—C4—C5—C6	2.4 (2)	C6—C5—N2—C1	177.41 (12)
N2—C5—C6—N1	−2.95 (18)	C4—C5—N2—Cu1	177.62 (11)
C4—C5—C6—N1	175.62 (12)	C6—C5—N2—Cu1	−3.86 (15)
N2—C5—C6—C7	179.11 (12)	O1—Cu1—N2—C1	10.63 (13)
C4—C5—C6—C7	−2.3 (2)	N1—Cu1—N2—C1	−175.03 (13)
N1—C6—C7—C8	0.6 (2)	O9—Cu1—N2—C1	−74.08 (13)
C5—C6—C7—C8	178.41 (12)	O3—Cu1—N2—C1	98.24 (12)
N1—C6—C7—C12	−177.39 (13)	O1—Cu1—N2—C5	−167.92 (9)
C5—C6—C7—C12	0.4 (2)	N1—Cu1—N2—C5	6.42 (9)
C6—C7—C8—C9	−2.3 (2)	O9—Cu1—N2—C5	107.37 (9)
C12—C7—C8—C9	175.64 (14)	O3—Cu1—N2—C5	−80.32 (9)
C7—C8—C9—C10	2.0 (2)	O6—Cl1—O3—Cu1	154.80 (8)
C8—C9—C10—N1	0.0 (2)	O4—Cl1—O3—Cu1	−82.19 (11)
C5—C4—C11—C12	−0.6 (2)	O5—Cl1—O3—Cu1	35.50 (10)
C3—C4—C11—C12	178.75 (14)	O2—Cu1—O3—Cl1	−49.19 (9)
C4—C11—C12—C7	−1.4 (2)	N2—Cu1—O3—Cl1	130.42 (9)
C6—C7—C12—C11	1.4 (2)	O1—Cu1—O3—Cl1	−137.86 (9)
C8—C7—C12—C11	−176.41 (14)	N1—Cu1—O3—Cl1	47.44 (9)
C9—C10—N1—C6	−1.7 (2)	O9—Cu1—O3—Cl1	−88.04 (19)
C9—C10—N1—Cu1	172.69 (11)	O10—Cl2—O9—Cu1	−134.98 (11)
C7—C6—N1—C10	1.3 (2)	O8—Cl2—O9—Cu1	−13.97 (13)
C5—C6—N1—C10	−176.52 (12)	O7—Cl2—O9—Cu1	104.93 (10)
C7—C6—N1—Cu1	−174.04 (11)	O2—Cu1—O9—Cl2	42.89 (10)
C5—C6—N1—Cu1	8.10 (14)	N2—Cu1—O9—Cl2	−137.45 (10)
O2—Cu1—N1—C10	−7.94 (14)	O1—Cu1—O9—Cl2	131.07 (10)
N2—Cu1—N1—C10	177.39 (13)	N1—Cu1—O9—Cl2	−53.38 (10)
O9—Cu1—N1—C10	83.79 (13)	O3—Cu1—O9—Cl2	81.01 (19)
O3—Cu1—N1—C10	−87.39 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O5^i	0.82 (2)	1.96 (2)	2.7619 (15)	166 (2)
O1—H1B···O7^ii	0.80 (2)	1.95 (2)	2.7486 (16)	175 (2)
O2—H2A···O5	0.83 (2)	1.95 (2)	2.7566 (16)	164 (2)
O2—H2B···O8	0.80 (2)	2.20 (2)	2.8339 (18)	136 (2)
O2—H2B···O8^iii	0.80 (2)	2.29 (2)	2.8802 (17)	132 (2)

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