Hexaaqua­copper(II) dichloride bis­(hexa­methyl­enetetra­mine) tetra­hydrate

Li, Z.L.; Yao, X.J.; Wu, W.; Xuan, Y.W.

doi:10.1107/S1600536808020916

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m1024

doi:10.1107/S1600536808020916

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Hexaaquacopper(II) dichloride bis(hexamethylenetetramine) tetrahydrate

Zhan Lin Li,^a Xin Jian Yao,^a Wen Wu ^a and Ya Wen Xuan ^a ^*

^aDepartment of Chemistry, Zhou Kou Normal University, Zhou Kou 466001, People's Republic of China
^*Correspondence e-mail: bookw@126.com

(Received 19 June 2008; accepted 7 July 2008; online 12 July 2008)

The title compound, [Cu(H₂O)₆]Cl₂·2C₆H₁₂N₄·4H₂O, was prepared under mild hydrothermal conditions. The asymmetric unit consists of one half of the [Cu(H₂O)₆]²⁺ cation, a hexamethylenetetramine molecule, two solvent water molecules and a chloride ion. The formula unit is generated by crystallographic inversion symmetry. The Cu atom lies on a crystallographic inversion centre. It is in a slightly distorted octahedral coordination environment. In the crystal structure, intermolecular O—H⋯O, O—H⋯N and O—H⋯Cl hydrogen bonds link the components into a three-dimensional network.

Related literature

For a related structure, see: Kinzhibalo et al. (2002 ).

Experimental

Crystal data

[Cu(H₂O)₆]Cl₂·2C₆H₁₂N₄·4H₂O
M_r = 594.99
Triclinic, $[P \overline 1]$
a = 9.321 (3) Å
b = 9.3923 (16) Å
c = 9.4261 (16) Å
α = 119.523 (2)°
β = 94.153 (3)°
γ = 101.065 (3)°
V = 691.1 (3) Å³
Z = 1
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 291 (2) K
0.36 × 0.29 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.709, T_max = 0.860
5328 measured reflections
2551 independent reflections
2083 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.108
S = 1.05
2551 reflections
151 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—O2	2.017 (2)
Cu1—O1	2.045 (2)
Cu1—O3	2.053 (2)

O2—Cu1—O2ⁱ	180
O2—Cu1—O1	87.24 (9)
O2—Cu1—O1ⁱ	92.76 (9)
O1—Cu1—O1ⁱ	180
O2—Cu1—O3ⁱ	90.30 (10)
O1—Cu1—O3ⁱ	86.64 (9)
O2—Cu1—O3	89.70 (10)
O1—Cu1—O3	93.36 (9)
O3ⁱ—Cu1—O3	180
Symmetry code: (i) -x+1, -y, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1W⋯N3	0.82	2.04	2.814 (3)	158
O1—H2W⋯O5ⁱⁱ	0.83	1.94	2.734 (3)	162
O2—H3W⋯N2ⁱⁱⁱ	0.83	1.99	2.800 (3)	167
O2—H4W⋯O4ⁱⁱⁱ	0.83	1.89	2.700 (3)	165
O3—H5W⋯Cl1	0.82	2.54	3.190 (2)	137
O3—H6W⋯N1^iv	0.82	2.00	2.805 (3)	165
O4—H7W⋯Cl1	0.83	2.35	3.170 (3)	168
O4—H8W⋯N4^v	0.84	2.00	2.829 (4)	174
O5—H9W⋯Cl1	0.83	2.43	3.245 (3)	169
O5—H10W⋯Cl1^vi	0.83	2.37	3.200 (3)	175
Symmetry codes: (ii) x, y, z-1; (iii) -x+1, -y+1, -z+1; (iv) x, y-1, z; (v) -x, -y+1, -z+1; (vi) -x, -y, -z+1.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020916/lh2645sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020916/lh2645Isup2.hkl

checkCIF report

Comment top

The asymmetric unit and some symmetry related atoms are shown in Fig.1. The asymmetric unit consists of one half of hexaaqua Cu^II cation, one chloride anion, one uncoordinated neutral hexamethylenetetramine molecule and two molecules of water of crystallization. In the crystal structure, hydrogen bonding between [Cu(H₂O)₆]²⁺ cations and hexamethylenetetramine molecules, and those between [Cu(H₂O)₆]²⁺ cations and chloride ions are shown in Fig. 2 and Fig.3, respectively. A 16-membered ring formed by cations and hexamethylenetetramine moieties via the H-bonding interactions propagates along the c-axis. The chloride ion H-bonded with the uncoordinated water molecules gives rise to a number of anionic ring systems (Fig. 3). One of the hydrogen atoms of the uncoordinated water molecule connects the chloride ion and forms a 16-membered ring. The combonation of these anionic and cationic frameworks results in the formation of a three-dimensional network.

Related literature top

For a related structure, see: Kinzhibalo et al. (2002).

Experimental top

All reagents were of AR grade and used without further purification. C₆H₁₂N₄ (1.401 g, 10 mmol) was dissolved in 50 ml EtOH/H₂O (V:V = 1:1) solution, then the resultant solution was added in 10 ml double-distilled water containing CuCl₂.2H₂O (0.171 g, 1 mmol), The resulting solution was heated at 373 K for 96 h. After cooling to room temperature, blue crystals were obtained in a yield up to 48.6%.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit and symmetry related atoms of the title compound with 30% probability ellipsoids [symmetry code: (A) -x+1, -y, -z].
	Fig. 2. Hydrogen bonding [dashed lines] in part of the crystal structure between [Cu(H₂O)₆]²⁺ cations, hexamethylenetetramine molecules and water molecules.
	Fig. 3. Hydrogen bonding [dashed lines] in part of the crystal structure between the [Cu(H₂O)₆]²⁺ cations, chloride anions and water molecules.

Hexaaquacopper(II) dichloride bis(hexamethylenetetramine) tetrahydrate top

Crystal data top

[Cu(H₂O)₆]Cl₂·2C₆H₁₂N₄·4H₂O	Z = 1
M_r = 594.99	F(000) = 315
Triclinic, P1	D_x = 1.430 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.321 (3) Å	Cell parameters from 1415 reflections
b = 9.3923 (16) Å	θ = 2.5–22.9°
c = 9.4261 (16) Å	µ = 1.04 mm⁻¹
α = 119.523 (2)°	T = 291 K
β = 94.153 (3)°	Block, blue
γ = 101.065 (3)°	0.36 × 0.29 × 0.15 mm
V = 691.1 (3) Å³

Data collection top

Bruker SMART CCD diffractometer	2551 independent reflections
Radiation source: fine-focus sealed tube	2083 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 0 pixels mm^-1	θ_max = 25.5°, θ_min = 2.5°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
T_min = 0.709, T_max = 0.860	l = −11→11
5328 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0473P)² + 0.4567P] P = (F_o² + 2F_c²)/3
2551 reflections	(Δ/σ)_max < 0.001
151 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Cu(H₂O)₆]Cl₂·2C₆H₁₂N₄·4H₂O	γ = 101.065 (3)°
M_r = 594.99	V = 691.1 (3) Å³
Triclinic, P1	Z = 1
a = 9.321 (3) Å	Mo Kα radiation
b = 9.3923 (16) Å	µ = 1.04 mm⁻¹
c = 9.4261 (16) Å	T = 291 K
α = 119.523 (2)°	0.36 × 0.29 × 0.15 mm
β = 94.153 (3)°

Data collection top

Bruker SMART CCD diffractometer	2551 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2083 reflections with I > 2σ(I)
T_min = 0.709, T_max = 0.860	R_int = 0.027
5328 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.06	Δρ_max = 0.30 e Å⁻³
2551 reflections	Δρ_min = −0.51 e Å⁻³
151 parameters

Special details top

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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 (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.5000	0.0000	0.0000	0.03048 (18)
Cl1	0.18946 (11)	0.17433 (12)	0.43516 (12)	0.0544 (3)
O1	0.3831 (2)	0.1341 (3)	−0.0575 (3)	0.0410 (6)
H1W	0.3885	0.2251	0.0267	0.061*
H2W	0.3032	0.0955	−0.1237	0.061*
O2	0.6183 (3)	0.2239 (3)	0.1983 (3)	0.0458 (6)
H3W	0.6168	0.2522	0.2960	0.069*
H4W	0.6825	0.2950	0.1926	0.069*
O3	0.3576 (3)	−0.0289 (3)	0.1457 (3)	0.0468 (6)
H5W	0.3400	0.0621	0.2072	0.070*
H6W	0.3653	−0.0847	0.1901	0.070*
O4	0.1965 (3)	0.5031 (3)	0.7782 (3)	0.0481 (6)
H7W	0.2086	0.4204	0.6934	0.072*
H8W	0.1057	0.4942	0.7787	0.072*
O5	0.1485 (3)	0.0517 (4)	0.7004 (4)	0.0741 (9)
H9W	0.1697	0.0946	0.6432	0.111*
H10W	0.0599	−0.0029	0.6717	0.111*
N1	0.3348 (3)	0.7402 (3)	0.2551 (3)	0.0349 (6)
N2	0.3362 (3)	0.6544 (3)	0.4602 (3)	0.0347 (6)
N3	0.3419 (3)	0.4512 (3)	0.1727 (3)	0.0339 (6)
N4	0.1150 (3)	0.5418 (3)	0.2441 (3)	0.0352 (6)
C1	0.3865 (4)	0.7928 (4)	0.4281 (4)	0.0372 (7)
H1A	0.3493	0.8884	0.5004	0.045*
H1B	0.4945	0.8297	0.4544	0.045*
C2	0.3940 (4)	0.5117 (4)	0.3491 (4)	0.0367 (7)
H2A	0.3622	0.4193	0.3685	0.044*
H2B	0.5021	0.5469	0.3747	0.044*
C3	0.1779 (4)	0.4020 (4)	0.1381 (4)	0.0399 (8)
H3A	0.1418	0.3631	0.0225	0.048*
H3B	0.1433	0.3083	0.1550	0.048*
C4	0.1704 (4)	0.6831 (4)	0.2180 (4)	0.0390 (8)
H4A	0.1311	0.7774	0.2886	0.047*
H4B	0.1342	0.6476	0.1034	0.047*
C5	0.3921 (4)	0.5949 (4)	0.1478 (4)	0.0384 (8)
H5A	0.5002	0.6301	0.1718	0.046*
H5B	0.3584	0.5583	0.0324	0.046*
C6	0.1729 (4)	0.5996 (4)	0.4188 (4)	0.0388 (8)
H6A	0.1335	0.6931	0.4911	0.047*
H6B	0.1386	0.5079	0.4386	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0393 (3)	0.0273 (3)	0.0255 (3)	0.0104 (2)	0.0087 (2)	0.0133 (2)
Cl1	0.0599 (6)	0.0441 (5)	0.0534 (6)	0.0137 (5)	0.0259 (5)	0.0190 (5)
O1	0.0505 (14)	0.0335 (12)	0.0335 (12)	0.0193 (11)	0.0002 (10)	0.0117 (10)
O2	0.0663 (16)	0.0310 (12)	0.0231 (11)	−0.0071 (11)	0.0028 (11)	0.0093 (10)
O3	0.0699 (17)	0.0442 (14)	0.0551 (15)	0.0328 (13)	0.0383 (13)	0.0372 (13)
O4	0.0416 (14)	0.0439 (14)	0.0435 (14)	0.0008 (11)	0.0087 (11)	0.0151 (12)
O5	0.0623 (18)	0.088 (2)	0.070 (2)	0.0023 (16)	−0.0133 (15)	0.0494 (19)
N1	0.0419 (16)	0.0337 (15)	0.0399 (15)	0.0157 (13)	0.0169 (12)	0.0237 (13)
N2	0.0422 (15)	0.0331 (14)	0.0248 (13)	0.0026 (12)	0.0077 (11)	0.0143 (12)
N3	0.0421 (15)	0.0299 (14)	0.0300 (14)	0.0139 (12)	0.0067 (12)	0.0141 (12)
N4	0.0353 (15)	0.0330 (15)	0.0333 (14)	0.0089 (12)	0.0074 (12)	0.0141 (12)
C1	0.0456 (19)	0.0255 (16)	0.0339 (17)	0.0049 (14)	0.0106 (15)	0.0117 (14)
C2	0.0448 (19)	0.0355 (18)	0.0335 (17)	0.0093 (15)	0.0032 (14)	0.0214 (15)
C3	0.0403 (19)	0.0323 (18)	0.0335 (18)	0.0067 (15)	0.0012 (15)	0.0090 (15)
C4	0.047 (2)	0.0410 (19)	0.0398 (18)	0.0225 (16)	0.0150 (15)	0.0240 (16)
C5	0.047 (2)	0.046 (2)	0.0327 (17)	0.0224 (17)	0.0174 (15)	0.0240 (16)
C6	0.048 (2)	0.0343 (18)	0.0359 (18)	0.0082 (15)	0.0176 (15)	0.0190 (15)

Geometric parameters (Å, º) top

Cu1—O2	2.017 (2)	N2—C2	1.469 (4)
Cu1—O2ⁱ	2.017 (2)	N2—C1	1.475 (4)
Cu1—O1	2.045 (2)	N3—C3	1.472 (4)
Cu1—O1ⁱ	2.045 (2)	N3—C2	1.473 (4)
Cu1—O3ⁱ	2.053 (2)	N3—C5	1.476 (4)
Cu1—O3	2.053 (2)	N4—C3	1.467 (4)
O1—H1W	0.8200	N4—C4	1.472 (4)
O1—H2W	0.8260	N4—C6	1.474 (4)
O2—H3W	0.8254	C1—H1A	0.9700
O2—H4W	0.8330	C1—H1B	0.9700
O3—H5W	0.8200	C2—H2A	0.9700
O3—H6W	0.8246	C2—H2B	0.9700
O4—H7W	0.8304	C3—H3A	0.9700
O4—H8W	0.8351	C3—H3B	0.9700
O5—H9W	0.8312	C4—H4A	0.9700
O5—H10W	0.8289	C4—H4B	0.9700
N1—C1	1.462 (4)	C5—H5A	0.9700
N1—C5	1.473 (4)	C5—H5B	0.9700
N1—C4	1.477 (4)	C6—H6A	0.9700
N2—C6	1.466 (4)	C6—H6B	0.9700

O2—Cu1—O2ⁱ	180	C4—N4—C6	107.7 (2)
O2—Cu1—O1	87.24 (9)	N1—C1—N2	111.9 (2)
O2ⁱ—Cu1—O1	92.76 (9)	N1—C1—H1A	109.2
O2—Cu1—O1ⁱ	92.76 (9)	N2—C1—H1A	109.2
O2ⁱ—Cu1—O1ⁱ	87.24 (9)	N1—C1—H1B	109.2
O1—Cu1—O1ⁱ	180	N2—C1—H1B	109.2
O2—Cu1—O3ⁱ	90.30 (10)	H1A—C1—H1B	107.9
O2ⁱ—Cu1—O3ⁱ	89.70 (10)	N2—C2—N3	112.0 (2)
O1—Cu1—O3ⁱ	86.64 (9)	N2—C2—H2A	109.2
O1ⁱ—Cu1—O3ⁱ	93.36 (9)	N3—C2—H2A	109.2
O2—Cu1—O3	89.70 (10)	N2—C2—H2B	109.2
O2ⁱ—Cu1—O3	90.30 (10)	N3—C2—H2B	109.2
O1—Cu1—O3	93.36 (9)	H2A—C2—H2B	107.9
O1ⁱ—Cu1—O3	86.64 (9)	N4—C3—N3	112.7 (3)
O3ⁱ—Cu1—O3	180	N4—C3—H3A	109.1
Cu1—O1—H1W	109.5	N3—C3—H3A	109.1
Cu1—O1—H2W	126.7	N4—C3—H3B	109.1
H1W—O1—H2W	113.2	N3—C3—H3B	109.1
Cu1—O2—H3W	124.5	H3A—C3—H3B	107.8
Cu1—O2—H4W	124.2	N4—C4—N1	112.3 (2)
H3W—O2—H4W	110.9	N4—C4—H4A	109.2
Cu1—O3—H5W	109.5	N1—C4—H4A	109.2
Cu1—O3—H6W	123.5	N4—C4—H4B	109.2
H5W—O3—H6W	113.5	N1—C4—H4B	109.2
H7W—O4—H8W	110.2	H4A—C4—H4B	107.9
H9W—O5—H10W	111.4	N1—C5—N3	112.0 (2)
C1—N1—C5	108.3 (2)	N1—C5—H5A	109.2
C1—N1—C4	108.1 (2)	N3—C5—H5A	109.2
C5—N1—C4	108.3 (3)	N1—C5—H5B	109.2
C6—N2—C2	108.5 (2)	N3—C5—H5B	109.2
C6—N2—C1	108.5 (2)	H5A—C5—H5B	107.9
C2—N2—C1	108.0 (2)	N2—C6—N4	112.1 (2)
C3—N3—C2	108.0 (3)	N2—C6—H6A	109.2
C3—N3—C5	108.1 (2)	N4—C6—H6A	109.2
C2—N3—C5	107.7 (2)	N2—C6—H6B	109.2
C3—N4—C4	108.1 (3)	N4—C6—H6B	109.2
C3—N4—C6	107.9 (2)	H6A—C6—H6B	107.9

C5—N1—C1—N2	−58.7 (3)	C3—N4—C4—N1	−57.9 (3)
C4—N1—C1—N2	58.3 (3)	C6—N4—C4—N1	58.4 (3)
C6—N2—C1—N1	−58.5 (3)	C1—N1—C4—N4	−58.8 (3)
C2—N2—C1—N1	58.9 (3)	C5—N1—C4—N4	58.3 (3)
C6—N2—C2—N3	58.4 (3)	C1—N1—C5—N3	58.7 (3)
C1—N2—C2—N3	−59.0 (3)	C4—N1—C5—N3	−58.2 (3)
C3—N3—C2—N2	−57.7 (3)	C3—N3—C5—N1	58.0 (3)
C5—N3—C2—N2	58.8 (3)	C2—N3—C5—N1	−58.5 (3)
C4—N4—C3—N3	58.1 (3)	C2—N2—C6—N4	−58.6 (3)
C6—N4—C3—N3	−58.2 (3)	C1—N2—C6—N4	58.5 (3)
C2—N3—C3—N4	58.1 (3)	C3—N4—C6—N2	58.2 (3)
C5—N3—C3—N4	−58.2 (3)	C4—N4—C6—N2	−58.3 (3)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1W···N3	0.82	2.04	2.814 (3)	158
O1—H2W···O5ⁱⁱ	0.83	1.94	2.734 (3)	162
O2—H3W···N2ⁱⁱⁱ	0.83	1.99	2.800 (3)	167
O2—H4W···O4ⁱⁱⁱ	0.83	1.89	2.700 (3)	165
O3—H5W···Cl1	0.82	2.54	3.190 (2)	137
O3—H6W···N1^iv	0.82	2.00	2.805 (3)	165
O4—H7W···Cl1	0.83	2.35	3.170 (3)	168
O4—H8W···N4^v	0.84	2.00	2.829 (4)	174
O5—H9W···Cl1	0.83	2.43	3.245 (3)	169
O5—H10W···Cl1^vi	0.83	2.37	3.200 (3)	175

Symmetry codes: (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x, y−1, z; (v) −x, −y+1, −z+1; (vi) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(H₂O)₆]Cl₂·2C₆H₁₂N₄·4H₂O
M_r	594.99
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	9.321 (3), 9.3923 (16), 9.4261 (16)
α, β, γ (°)	119.523 (2), 94.153 (3), 101.065 (3)
V (Å³)	691.1 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.36 × 0.29 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.709, 0.860
No. of measured, independent and observed [I > 2σ(I)] reflections	5328, 2551, 2083
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.108, 1.06
No. of reflections	2551
No. of parameters	151
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.51

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—O2	2.017 (2)	Cu1—O3	2.053 (2)
Cu1—O1	2.045 (2)

O2—Cu1—O2ⁱ	180	O1—Cu1—O3ⁱ	86.64 (9)
O2—Cu1—O1	87.24 (9)	O2—Cu1—O3	89.70 (10)
O2—Cu1—O1ⁱ	92.76 (9)	O1—Cu1—O3	93.36 (9)
O1—Cu1—O1ⁱ	180	O3ⁱ—Cu1—O3	180
O2—Cu1—O3ⁱ	90.30 (10)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1W···N3	0.82	2.04	2.814 (3)	157.8
O1—H2W···O5ⁱⁱ	0.83	1.94	2.734 (3)	162.1
O2—H3W···N2ⁱⁱⁱ	0.83	1.99	2.800 (3)	166.5
O2—H4W···O4ⁱⁱⁱ	0.83	1.89	2.700 (3)	164.7
O3—H5W···Cl1	0.82	2.54	3.190 (2)	136.7
O3—H6W···N1^iv	0.82	2.00	2.805 (3)	165.0
O4—H7W···Cl1	0.83	2.35	3.170 (3)	168.1
O4—H8W···N4^v	0.84	2.00	2.829 (4)	174.4
O5—H9W···Cl1	0.83	2.43	3.245 (3)	168.5
O5—H10W···Cl1^vi	0.83	2.37	3.200 (3)	174.8

Symmetry codes: (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x, y−1, z; (v) −x, −y+1, −z+1; (vi) −x, −y, −z+1.

Acknowledgements

We thank the Natural Science Foundation of Henan Province and the Key Discipline Foundation of Zhoukou Normal University for financial support of this research.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kinzhibalo, V. V., Mys'kiv, M. G. & Davydov, V. N. (2002). Koord. Khim. 28, 927–928. 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