Bis(N,N-diisopropyl­butanaminium) bis­[di-μ-chlorido-bis­[dichlorido­cuprate(II)]]

Dai, J.; Xu, J.

doi:10.1107/S1600536810054280

metal-organic compounds

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Volume 67| Part 2| February 2011| Page m170

doi:10.1107/S1600536810054280

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Bis(N,N-diisopropylbutanaminium) bis[di-μ-chlorido-bis[dichloridocuprate(II)]]

Jing Dai ^a ^* and Jie Xu ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fudavid88@yahoo.com.cn

(Received 20 December 2010; accepted 25 December 2010; online 15 January 2011)

In the title compound, (C₁₀H₂₄N)₂[Cu₂Cl₆], N,N-diisopropylbutanamine is protonated on the N atom. The Cu^II atom in the centrosymmetric [Cu₂Cl₆]²⁻ anion has a distorted tetrahedral geometry. In the crystal, the cations and anions are connected by N—H⋯Cl and C—H⋯Cl hydrogen bonds into layers parallel to (100).

Related literature

For the properties and structures of N,N-diisopropylbutyl-1-amine compounds, see: Fu et al. (2007 , 2008 , 2009 ); Fu & Xiong (2008 ).

Experimental

Crystal data

(C₁₀H₂₄N)₂[Cu₂Cl₆]
M_r = 656.40
Triclinic, $[P \overline 1]$
a = 8.5697 (17) Å
b = 10.213 (2) Å
c = 10.384 (2) Å
α = 72.43 (3)°
β = 68.53 (3)°
γ = 71.78 (3)°
V = 785.1 (3) Å³
Z = 1
Mo Kα radiation
μ = 1.88 mm⁻¹
T = 298 K
0.30 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.910, T_max = 1.000
8206 measured reflections
3588 independent reflections
2728 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.107
S = 1.08
3588 reflections
141 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl3	0.91	2.44	3.336 (3)	168
C2—H2A⋯Cl3ⁱ	0.98	2.82	3.668 (5)	146
C5—H5A⋯Cl2ⁱⁱ	0.98	2.64	3.511 (4)	149
C8—H8A⋯Cl3	0.97	2.78	3.617 (4)	144
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z+2.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054280/hy2392sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054280/hy2392Isup2.hkl

checkCIF report

Comment top

Salts of amide have attracted more attention as phase transition dielectric materials for its applications in memory storage (Fu et al., 2007, 2008, 2009; Fu & Xiong, 2008). With the purpose of obtaining phase transition crystals of N,N-diisopropylbutyl-1-amine salts, its interactions with various metal ions have been studied and we have elaborated a series of new materials with this organic molecule. In this paper, we describe the crystal structure of the title compound,

The asymmetric unit is composed of half [Cu₂Cl₆]^2- anion and one [C₁₀H₂₄N]⁺ cation (Fig. 1). The N atom of N,N-diisopropylbutyl-1-amine is protonated, thus indicating one positive charge in the amide N atom. The half [Cu₂Cl₆]^2- anion showing one negative charge makes charge balance. The geometric parameters of the title compound are in a normal range. In the crystal structure, the cations and anions are involved in N—H···Cl and C—H···Cl hydrogen bonds (Table 1), which link the cations and anions into a two-dimensional network (Fig. 2).

Related literature top

For the properties and structures of N,N-diisopropylbutyl-1-amine compounds, see: Fu et al. (2007, 2008, 2009); Fu & Xiong (2008).

Experimental top

The commercial N,N-diisopropylbutyl-1-amine (10 mmol), HCl (2 ml) and CuCl₂ (5 mmol) were dissolved in 10 ml water. The solvent was slowly evaporated in air, affording blue block-shaped crystals of the title compound suitable for X-ray analysis.

The dielectric constant of the title compound as a function of temperature indicates that the permittivity is basically temperature-independent, suggesting that this compound should not be a real ferroelectrics or there may be no distinct phase transition occurred within the measured temperature range. Similarly, below the melting point (446–447 K) of the compound, the dielectric constant as a function of temperature also goes smoothly, and there is no dielectric anomaly observed (dielectric constant equaling to 8.9 to 10.6).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (A) 1-x, 2-y, 1-z.]
	Fig. 2. The crystal packing of the title compound, showing the two-dimensional network. Dashed lines denote hydrogen bonds.

Bis(N,N-diisopropylbutanaminium) bis[di-µ-chlorido-bis[dichloridocuprate(II)]] top

Crystal data top

(C₁₀H₂₄N)₂[Cu₂Cl₆]	Z = 1
M_r = 656.40	F(000) = 342
Triclinic, P1	D_x = 1.388 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5697 (17) Å	Cell parameters from 3588 reflections
b = 10.213 (2) Å	θ = 3.4–27.5°
c = 10.384 (2) Å	µ = 1.88 mm⁻¹
α = 72.43 (3)°	T = 298 K
β = 68.53 (3)°	Block, blue
γ = 71.78 (3)°	0.30 × 0.05 × 0.05 mm
V = 785.1 (3) Å³

Data collection top

Rigaku Mercury2 CCD diffractometer	3588 independent reflections
Radiation source: fine-focus sealed tube	2728 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
T_min = 0.910, T_max = 1.000	l = −13→13
8206 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0342P)² + 0.4528P] where P = (F_o² + 2F_c²)/3
3588 reflections	(Δ/σ)_max < 0.001
141 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

(C₁₀H₂₄N)₂[Cu₂Cl₆]	γ = 71.78 (3)°
M_r = 656.40	V = 785.1 (3) Å³
Triclinic, P1	Z = 1
a = 8.5697 (17) Å	Mo Kα radiation
b = 10.213 (2) Å	µ = 1.88 mm⁻¹
c = 10.384 (2) Å	T = 298 K
α = 72.43 (3)°	0.30 × 0.05 × 0.05 mm
β = 68.53 (3)°

Data collection top

Rigaku Mercury2 CCD diffractometer	3588 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2728 reflections with I > 2σ(I)
T_min = 0.910, T_max = 1.000	R_int = 0.044
8206 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.08	Δρ_max = 0.45 e Å⁻³
3588 reflections	Δρ_min = −0.52 e Å⁻³
141 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.7275 (3)	0.3131 (3)	0.7043 (3)	0.0374 (6)
H1	0.7197	0.4066	0.6644	0.045*
C1	0.5308 (7)	0.1423 (5)	0.8060 (6)	0.0907 (17)
H1A	0.4248	0.1297	0.8051	0.136*
H1B	0.5300	0.1267	0.9021	0.136*
H1C	0.6256	0.0761	0.7589	0.136*
Cu1	0.55821 (5)	0.83754 (4)	0.59096 (4)	0.03888 (14)
Cl1	0.30886 (11)	1.01180 (9)	0.60170 (11)	0.0629 (3)
C2	0.5495 (4)	0.2903 (4)	0.7304 (4)	0.0510 (9)
H2A	0.5344	0.3062	0.6374	0.061*
Cl2	0.50922 (16)	0.75177 (13)	0.81673 (10)	0.0778 (4)
C3	0.4106 (5)	0.3995 (5)	0.8062 (5)	0.0680 (12)
H3A	0.3011	0.4003	0.8002	0.102*
H3B	0.4357	0.4909	0.7625	0.102*
H3C	0.4069	0.3766	0.9038	0.102*
Cl3	0.70329 (12)	0.64171 (9)	0.51116 (9)	0.0505 (2)
C4	0.8746 (6)	0.4013 (5)	0.8158 (4)	0.0663 (12)
H4A	0.8994	0.3922	0.9015	0.099*
H4B	0.8065	0.4941	0.7912	0.099*
H4C	0.9805	0.3864	0.7407	0.099*
C5	0.7756 (4)	0.2922 (4)	0.8379 (4)	0.0449 (8)
H5A	0.6679	0.3114	0.9140	0.054*
C6	0.8723 (6)	0.1434 (4)	0.8862 (4)	0.0707 (13)
H6A	0.8802	0.1331	0.9787	0.106*
H6B	0.9860	0.1261	0.8209	0.106*
H6C	0.8119	0.0771	0.8894	0.106*
C7	0.8673 (4)	0.2391 (4)	0.5948 (3)	0.0447 (8)
H7A	0.8709	0.1389	0.6258	0.054*
H7B	0.9768	0.2520	0.5902	0.054*
C8	0.8484 (5)	0.2876 (4)	0.4479 (3)	0.0452 (8)
H8A	0.8366	0.3890	0.4183	0.054*
H8B	0.7446	0.2670	0.4494	0.054*
C9	1.0015 (5)	0.2162 (4)	0.3426 (4)	0.0565 (10)
H9A	1.1046	0.2375	0.3417	0.068*
H9B	1.0137	0.1149	0.3740	0.068*
C10	0.9891 (6)	0.2596 (5)	0.1937 (4)	0.0698 (12)
H10A	1.0904	0.2107	0.1328	0.105*
H10B	0.9796	0.3595	0.1607	0.105*
H10C	0.8893	0.2364	0.1929	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0384 (15)	0.0359 (14)	0.0347 (15)	−0.0041 (11)	−0.0109 (12)	−0.0078 (12)
C1	0.083 (3)	0.072 (3)	0.124 (5)	−0.045 (3)	−0.018 (3)	−0.016 (3)
Cu1	0.0400 (2)	0.0323 (2)	0.0370 (2)	−0.00387 (16)	−0.00747 (17)	−0.00665 (17)
Cl1	0.0393 (5)	0.0424 (5)	0.0699 (7)	−0.0006 (4)	0.0065 (4)	0.0027 (4)
C2	0.043 (2)	0.066 (2)	0.047 (2)	−0.0150 (18)	−0.0124 (17)	−0.0148 (19)
Cl2	0.0893 (8)	0.0808 (8)	0.0353 (5)	−0.0012 (6)	−0.0073 (5)	−0.0061 (5)
C3	0.040 (2)	0.084 (3)	0.070 (3)	−0.007 (2)	−0.009 (2)	−0.019 (2)
Cl3	0.0628 (6)	0.0332 (4)	0.0488 (5)	−0.0008 (4)	−0.0151 (4)	−0.0118 (4)
C4	0.073 (3)	0.083 (3)	0.058 (3)	−0.023 (2)	−0.031 (2)	−0.017 (2)
C5	0.0412 (19)	0.053 (2)	0.0355 (19)	−0.0014 (16)	−0.0136 (15)	−0.0097 (16)
C6	0.084 (3)	0.065 (3)	0.054 (3)	0.011 (2)	−0.039 (2)	−0.005 (2)
C7	0.0429 (19)	0.0426 (19)	0.042 (2)	0.0019 (15)	−0.0118 (16)	−0.0134 (16)
C8	0.051 (2)	0.0408 (19)	0.044 (2)	−0.0037 (16)	−0.0172 (17)	−0.0138 (16)
C9	0.057 (2)	0.062 (2)	0.046 (2)	−0.0047 (19)	−0.0102 (18)	−0.0212 (19)
C10	0.081 (3)	0.083 (3)	0.049 (2)	−0.017 (2)	−0.012 (2)	−0.030 (2)

Geometric parameters (Å, º) top

N1—C7	1.501 (4)	C4—H4B	0.9600
N1—C5	1.525 (4)	C4—H4C	0.9600
N1—C2	1.528 (4)	C5—C6	1.518 (5)
N1—H1	0.9100	C5—H5A	0.9800
C1—C2	1.506 (5)	C6—H6A	0.9600
C1—H1A	0.9600	C6—H6B	0.9600
C1—H1B	0.9600	C6—H6C	0.9600
C1—H1C	0.9600	C7—C8	1.508 (4)
Cu1—Cl2	2.1701 (13)	C7—H7A	0.9700
Cu1—Cl3	2.2190 (12)	C7—H7B	0.9700
Cu1—Cl1ⁱ	2.2884 (14)	C8—C9	1.511 (5)
Cu1—Cl1	2.3051 (13)	C8—H8A	0.9700
Cl1—Cu1ⁱ	2.2884 (14)	C8—H8B	0.9700
C2—C3	1.515 (5)	C9—C10	1.509 (5)
C2—H2A	0.9800	C9—H9A	0.9700
C3—H3A	0.9600	C9—H9B	0.9700
C3—H3B	0.9600	C10—H10A	0.9600
C3—H3C	0.9600	C10—H10B	0.9600
C4—C5	1.519 (5)	C10—H10C	0.9600
C4—H4A	0.9600

C7—N1—C5	113.3 (2)	C6—C5—C4	111.9 (3)
C7—N1—C2	113.5 (3)	C6—C5—N1	113.9 (3)
C5—N1—C2	114.8 (3)	C4—C5—N1	109.1 (3)
C7—N1—H1	104.6	C6—C5—H5A	107.2
C5—N1—H1	104.6	C4—C5—H5A	107.2
C2—N1—H1	104.6	N1—C5—H5A	107.2
C2—C1—H1A	109.5	C5—C6—H6A	109.5
C2—C1—H1B	109.5	C5—C6—H6B	109.5
H1A—C1—H1B	109.5	H6A—C6—H6B	109.5
C2—C1—H1C	109.5	C5—C6—H6C	109.5
H1A—C1—H1C	109.5	H6A—C6—H6C	109.5
H1B—C1—H1C	109.5	H6B—C6—H6C	109.5
Cl2—Cu1—Cl3	99.48 (5)	N1—C7—C8	115.2 (3)
Cl2—Cu1—Cl1ⁱ	146.21 (6)	N1—C7—H7A	108.5
Cl3—Cu1—Cl1ⁱ	96.22 (5)	C8—C7—H7A	108.5
Cl2—Cu1—Cl1	97.69 (6)	N1—C7—H7B	108.5
Cl3—Cu1—Cl1	143.17 (5)	C8—C7—H7B	108.5
Cl1ⁱ—Cu1—Cl1	87.01 (5)	H7A—C7—H7B	107.5
Cu1ⁱ—Cl1—Cu1	92.99 (5)	C7—C8—C9	111.6 (3)
C1—C2—C3	112.0 (4)	C7—C8—H8A	109.3
C1—C2—N1	113.3 (3)	C9—C8—H8A	109.3
C3—C2—N1	110.3 (3)	C7—C8—H8B	109.3
C1—C2—H2A	107.0	C9—C8—H8B	109.3
C3—C2—H2A	107.0	H8A—C8—H8B	108.0
N1—C2—H2A	107.0	C10—C9—C8	114.0 (3)
C2—C3—H3A	109.5	C10—C9—H9A	108.8
C2—C3—H3B	109.5	C8—C9—H9A	108.8
H3A—C3—H3B	109.5	C10—C9—H9B	108.8
C2—C3—H3C	109.5	C8—C9—H9B	108.8
H3A—C3—H3C	109.5	H9A—C9—H9B	107.6
H3B—C3—H3C	109.5	C9—C10—H10A	109.5
C5—C4—H4A	109.5	C9—C10—H10B	109.5
C5—C4—H4B	109.5	H10A—C10—H10B	109.5
H4A—C4—H4B	109.5	C9—C10—H10C	109.5
C5—C4—H4C	109.5	H10A—C10—H10C	109.5
H4A—C4—H4C	109.5	H10B—C10—H10C	109.5
H4B—C4—H4C	109.5

Cl2—Cu1—Cl1—Cu1ⁱ	146.38 (6)	C2—N1—C5—C6	92.1 (4)
Cl3—Cu1—Cl1—Cu1ⁱ	−96.39 (7)	C7—N1—C5—C4	85.3 (4)
Cl1ⁱ—Cu1—Cl1—Cu1ⁱ	0.0	C2—N1—C5—C4	−142.1 (3)
C7—N1—C2—C1	70.5 (4)	C5—N1—C7—C8	−163.7 (3)
C5—N1—C2—C1	−62.1 (4)	C2—N1—C7—C8	63.0 (4)
C7—N1—C2—C3	−163.1 (3)	N1—C7—C8—C9	175.3 (3)
C5—N1—C2—C3	64.3 (4)	C7—C8—C9—C10	179.4 (3)
C7—N1—C5—C6	−40.5 (4)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl3	0.91	2.44	3.336 (3)	168
C2—H2A···Cl3ⁱⁱ	0.98	2.82	3.668 (5)	146
C5—H5A···Cl2ⁱⁱⁱ	0.98	2.64	3.511 (4)	149
C8—H8A···Cl3	0.97	2.78	3.617 (4)	144

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

Experimental details

Crystal data
Chemical formula	(C₁₀H₂₄N)₂[Cu₂Cl₆]
M_r	656.40
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.5697 (17), 10.213 (2), 10.384 (2)
α, β, γ (°)	72.43 (3), 68.53 (3), 71.78 (3)
V (Å³)	785.1 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.88
Crystal size (mm)	0.30 × 0.05 × 0.05

Data collection
Diffractometer	Rigaku Mercury2 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.910, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8206, 3588, 2728
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.107, 1.08
No. of reflections	3588
No. of parameters	141
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.52

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl3	0.91	2.44	3.336 (3)	168
C2—H2A···Cl3ⁱ	0.98	2.82	3.668 (5)	146
C5—H5A···Cl2ⁱⁱ	0.98	2.64	3.511 (4)	149
C8—H8A···Cl3	0.97	2.78	3.617 (4)	144

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

Acknowledgements

This work was supported by a start-up grant from Southeast University, China.

References

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis(N,N-diiso­propyl­butanaminium) bis­­[di-μ-chlorido-bis­­[di­chlorido­cuprate(II)]]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(N,N-diisopropylbutanaminium) bis[di-μ-chlorido-bis[dichloridocuprate(II)]]