[μ-2,2′-(1,4-Phenyl­ene)diacetato-κ2O1:O4]bis­[aqua­(2,2′-bipyridine-κ2N,N′)chloridocopper(II)] dihydrate

Zhao, J.-H.; Lin, Y.-X.; Wu, W.; Zhang, Z.

doi:10.1107/S1600536812029686

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page m1114

https://doi.org/10.1107/S1600536812029686

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[μ-2,2′-(1,4-Phenylene)diacetato-κ²O¹:O⁴]bis[aqua(2,2′-bipyridine-κ²N,N′)chloridocopper(II)] dihydrate

Jin-He Zhao,^a ^* Yan-Xia Lin,^b Wei Wu ^c and Zhong Zhang ^c

^aDepartment of Chemical and Life Science, Baise University, Baise 533000, People's Republic of China, ^bHybio Pharmaceutical Co. Ltd, Shenzhen 518057, People's Republic of China, and ^cDepartment of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Nanning 530006, People's Republic of China
^*Correspondence e-mail: tougaomingda@163.com

(Received 25 June 2012; accepted 29 June 2012; online 25 July 2012)

In the centrosymmetric title compound, [Cu₂(C₁₀H₈O₄)Cl₂(C₁₀H₈N₂)₂(H₂O)₂]·2H₂O, the Cu^II atom is five-coordinated in a distorted square-pyramidal geometry by two N atoms from a chelating 2,2′-bipyridine ligand, one O atom from a 1,4-phenylenediacetate ligand, one Cl atom and one water molecule. The 1,4-phenylenediacetate ligand, lying on an inversion center, bridges two Cu^II atoms. In the crystal, O—H⋯O and O—H⋯Cl hydrogen bonds and π–π interactions between the pyridine rings [centroid–centroid distance = 3.740 (5) Å] link the complex molecules and uncoordinated water molecules into a three-dimensional network.

Related literature

For related structures, see: Hu et al. (2009 ); Wu et al. (2010 , 2011 ).

Experimental

Crystal data

[Cu₂(C₁₀H₈O₄)Cl₂(C₁₀H₈N₂)₂(H₂O)₂]·2H₂O
M_r = 774.58
Monoclinic, P 2₁ /c
a = 11.713 (4) Å
b = 6.954 (2) Å
c = 19.585 (7) Å
β = 100.507 (5)°
V = 1568.6 (9) Å³
Z = 2
Mo Kα radiation
μ = 1.58 mm⁻¹
T = 296 K
0.41 × 0.39 × 0.37 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.563, T_max = 0.592
7958 measured reflections
3011 independent reflections
2394 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.083
wR(F²) = 0.177
S = 1.06
3011 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ⁱ	0.85	2.00	2.822 (8)	164
O3—H3B⋯O4ⁱⁱ	0.85	1.94	2.769 (8)	164
O4—H4A⋯O1	0.85	2.06	2.900 (8)	169
O4—H4B⋯Cl1ⁱⁱ	0.85	2.44	3.276 (7)	169
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812029686/hy2565sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029686/hy2565Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029686/hy2565Isup3.cdx

checkCIF report

Comment top

2,2'-Bipyridine (2,2'-bpy) is one of the first-line popular drugs used to treat invasive infections. 1,4-Phenylenediacetic acid (H₂PDA) has two flexible acetate groups, resulting in trans- or cis-conformation. Both of them are interesting candidates to coordinate to metal ions through nitrogen atoms or oxygen atoms for constructing a diversity of coordination architectures (Hu et al., 2009; Wu et al., 2010, 2011).

In the title complex (Fig. 1), the Cu^II atom is five-coordinated by two N atoms (N1, N2) from a 2,2-bpy ligand, one O atom (O1) from a centrosymmetric PDA ligand, one O atom (O3) from a water molecule and one chloride ion. The asymmetric unit also contains one uncoordinated water molecule. O—H···O and O—H···Cl hydrogen bonds (Table 1) and π–π interactions between the pyridine rings [centroid–centroid distance = 3.740 (5) Å] result in the formation of a supramolecular structure (Fig. 2).

Related literature top

For related structures, see: Hu et al. (2009); Wu et al. (2010, 2011).

Experimental top

1,4-Phenylenediacetic acid (0.097 g, 0.5 mmol) and 2,2-bipyridine (0.078 g, 0.5 mmol) were dissolved in a mixture of 15 ml N,N-dimethylformamide and 10 ml water and an aqueous solution of sodium hydroxide was added dropwise with stirring to adjust the pH value being 6. Then 5 ml aqueous solution of CuCl₂.2H₂O (0.097 g, 0.05 mmol) was added. The mixture was kept stirring at 350 K for 4 h and then filtered. The filtrate was kept at room temperature and a few days later X-ray quality blue block-shaped crystals were obtained. Analysis, calculated for C₃₀H₃₂Cl₂Cu₂N₄O₈: C 46.52, H 4.16, N 7.23%; found: C 46.49, H 4.17, N 7.21%.

Structure description top

For related structures, see: Hu et al. (2009); Wu et al. (2010, 2011).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability ellipsoids. [Symmetry code: (a) 1-x, -y, 1-z.]
	Fig. 2. Crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines.

[µ-2,2'-(1,4-Phenylene)diacetato-κ²O¹:O⁴]bis[aqua(2,2'- bipyridine-κ²N,N')chloridocopper(II)] dihydrate top

Crystal data top

[Cu₂(C₁₀H₈O₄)Cl₂(C₁₀H₈N₂)₂(H₂O)₂]·2H₂O	F(000) = 792
M_r = 774.58	D_x = 1.640 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3637 reflections
a = 11.713 (4) Å	θ = 2.5–28.2°
b = 6.954 (2) Å	µ = 1.58 mm⁻¹
c = 19.585 (7) Å	T = 296 K
β = 100.507 (5)°	Block, blue
V = 1568.6 (9) Å³	0.41 × 0.39 × 0.37 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD diffractometer	3011 independent reflections
Radiation source: fine-focus sealed tube	2394 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.563, T_max = 0.592	k = −8→8
7958 measured reflections	l = −23→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.083	H-atom parameters constrained
wR(F²) = 0.177	w = 1/[σ²(F_o²) + (0.0067P)² + 24.0162P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3011 reflections	Δρ_max = 0.92 e Å⁻³
209 parameters	Δρ_min = −0.79 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0220 (15)

Crystal data top

[Cu₂(C₁₀H₈O₄)Cl₂(C₁₀H₈N₂)₂(H₂O)₂]·2H₂O	V = 1568.6 (9) Å³
M_r = 774.58	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.713 (4) Å	µ = 1.58 mm⁻¹
b = 6.954 (2) Å	T = 296 K
c = 19.585 (7) Å	0.41 × 0.39 × 0.37 mm
β = 100.507 (5)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3011 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2394 reflections with I > 2σ(I)
T_min = 0.563, T_max = 0.592	R_int = 0.039
7958 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	0 restraints
wR(F²) = 0.177	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0067P)² + 24.0162P] where P = (F_o² + 2F_c²)/3
3011 reflections	Δρ_max = 0.92 e Å⁻³
209 parameters	Δρ_min = −0.79 e Å⁻³

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 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 (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.77380 (7)	0.64270 (13)	0.35400 (4)	0.0243 (3)
Cl1	0.71866 (18)	0.5594 (4)	0.24104 (10)	0.0431 (6)
N1	0.9450 (5)	0.6443 (10)	0.3524 (3)	0.0313 (14)
N2	0.8374 (5)	0.7190 (9)	0.4531 (3)	0.0281 (14)
O1	0.6232 (4)	0.5601 (8)	0.3742 (3)	0.0295 (12)
O2	0.7159 (4)	0.2915 (8)	0.4109 (3)	0.0345 (13)
O3	0.7324 (6)	0.9562 (8)	0.3321 (3)	0.0473 (16)
H3A	0.7360	1.0454	0.3620	0.057*
H3B	0.6885	0.9940	0.2951	0.057*
O4	0.4144 (6)	0.6431 (10)	0.2741 (3)	0.0547 (18)
H4A	0.4750	0.6346	0.3053	0.066*
H4B	0.3871	0.7562	0.2748	0.066*
C1	0.9972 (8)	0.6049 (13)	0.2969 (4)	0.041 (2)
H1	0.9499	0.5767	0.2546	0.049*
C2	1.1147 (8)	0.6046 (15)	0.2998 (5)	0.048 (2)
H2	1.1470	0.5736	0.2612	0.057*
C3	1.1824 (7)	0.6517 (14)	0.3616 (4)	0.041 (2)
H3	1.2625	0.6590	0.3649	0.050*
C4	1.1348 (7)	0.6885 (12)	0.4192 (4)	0.0337 (18)
H4	1.1818	0.7147	0.4618	0.040*
C5	1.0153 (6)	0.6858 (9)	0.4124 (4)	0.0235 (15)
C6	0.9531 (6)	0.7264 (10)	0.4706 (4)	0.0224 (15)
C7	1.0085 (7)	0.7747 (11)	0.5371 (4)	0.0295 (17)
H7	1.0891	0.7797	0.5483	0.035*
C8	0.9419 (8)	0.8147 (11)	0.5861 (4)	0.0360 (19)
H8	0.9771	0.8440	0.6313	0.043*
C9	0.8234 (7)	0.8113 (13)	0.5681 (4)	0.039 (2)
H9	0.7774	0.8423	0.6005	0.047*
C10	0.7729 (6)	0.7610 (12)	0.5006 (4)	0.0318 (17)
H10	0.6924	0.7565	0.4884	0.038*
C11	0.6254 (6)	0.3871 (10)	0.3943 (3)	0.0240 (15)
C12	0.5077 (6)	0.2956 (12)	0.3957 (4)	0.0316 (18)
H12A	0.4540	0.3965	0.4031	0.038*
H12B	0.4790	0.2399	0.3504	0.038*
C13	0.5059 (6)	0.1417 (11)	0.4501 (4)	0.0245 (15)
C14	0.5399 (7)	0.1820 (11)	0.5198 (4)	0.0330 (18)
H14	0.5661	0.3047	0.5336	0.040*
C15	0.4647 (6)	−0.0410 (11)	0.4305 (4)	0.0282 (16)
H15	0.4399	−0.0693	0.3838	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0217 (5)	0.0281 (5)	0.0225 (5)	−0.0032 (4)	0.0024 (3)	−0.0004 (4)
Cl1	0.0393 (11)	0.0609 (14)	0.0257 (10)	−0.0081 (10)	−0.0029 (8)	−0.0083 (9)
N1	0.034 (3)	0.033 (3)	0.026 (3)	−0.004 (3)	0.003 (3)	0.006 (3)
N2	0.027 (3)	0.030 (3)	0.026 (3)	−0.003 (3)	0.002 (3)	−0.001 (3)
O1	0.021 (3)	0.033 (3)	0.033 (3)	−0.001 (2)	0.002 (2)	0.004 (2)
O2	0.029 (3)	0.034 (3)	0.039 (3)	0.002 (2)	0.002 (2)	0.007 (2)
O3	0.074 (4)	0.028 (3)	0.037 (3)	0.013 (3)	0.002 (3)	0.002 (3)
O4	0.053 (4)	0.044 (4)	0.058 (4)	0.008 (3)	−0.014 (3)	−0.003 (3)
C1	0.045 (5)	0.051 (5)	0.025 (4)	−0.004 (4)	0.004 (4)	0.001 (4)
C2	0.038 (5)	0.069 (7)	0.041 (5)	−0.004 (5)	0.018 (4)	0.005 (5)
C3	0.025 (4)	0.061 (6)	0.035 (4)	−0.004 (4)	−0.002 (3)	0.007 (4)
C4	0.027 (4)	0.040 (5)	0.033 (4)	−0.001 (3)	0.003 (3)	−0.003 (4)
C5	0.022 (3)	0.016 (3)	0.032 (4)	−0.005 (3)	0.005 (3)	0.005 (3)
C6	0.020 (3)	0.020 (3)	0.026 (4)	0.003 (3)	0.000 (3)	0.002 (3)
C7	0.029 (4)	0.028 (4)	0.028 (4)	−0.007 (3)	−0.004 (3)	0.000 (3)
C8	0.053 (5)	0.031 (4)	0.023 (4)	0.004 (4)	0.003 (3)	−0.007 (3)
C9	0.039 (5)	0.047 (5)	0.035 (4)	0.001 (4)	0.018 (4)	−0.010 (4)
C10	0.023 (4)	0.042 (5)	0.031 (4)	0.002 (3)	0.007 (3)	0.002 (4)
C11	0.036 (4)	0.021 (4)	0.014 (3)	−0.005 (3)	0.000 (3)	0.001 (3)
C12	0.023 (4)	0.041 (4)	0.026 (4)	−0.012 (3)	−0.009 (3)	0.003 (3)
C13	0.018 (3)	0.034 (4)	0.022 (3)	−0.002 (3)	0.007 (3)	0.005 (3)
C14	0.043 (5)	0.024 (4)	0.032 (4)	−0.002 (3)	0.006 (3)	−0.006 (3)
C15	0.029 (4)	0.033 (4)	0.021 (3)	−0.010 (3)	0.001 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Cu1—O1	1.963 (5)	C4—C5	1.383 (10)
Cu1—N1	2.011 (6)	C4—H4	0.9300
Cu1—N2	2.020 (6)	C5—C6	1.487 (10)
Cu1—O3	2.257 (6)	C6—C7	1.387 (9)
Cu1—Cl1	2.264 (2)	C7—C8	1.369 (11)
N1—C5	1.338 (9)	C7—H7	0.9300
N1—C1	1.368 (10)	C8—C9	1.368 (12)
N2—C10	1.333 (10)	C8—H8	0.9300
N2—C6	1.338 (9)	C9—C10	1.391 (11)
O1—C11	1.265 (8)	C9—H9	0.9300
O2—C11	1.243 (9)	C10—H10	0.9300
O3—H3A	0.8500	C11—C12	1.523 (10)
O3—H3B	0.8500	C12—C13	1.513 (10)
O4—H4A	0.8500	C12—H12A	0.9700
O4—H4B	0.8500	C12—H12B	0.9700
C1—C2	1.367 (12)	C13—C14	1.379 (10)
C1—H1	0.9300	C13—C15	1.388 (10)
C2—C3	1.361 (12)	C14—C15ⁱ	1.389 (11)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.369 (11)	C15—C14ⁱ	1.389 (11)
C3—H3	0.9300	C15—H15	0.9300

O1—Cu1—N1	160.0 (2)	C4—C5—C6	123.6 (7)
O1—Cu1—N2	94.1 (2)	N2—C6—C7	121.9 (7)
N1—Cu1—N2	79.6 (3)	N2—C6—C5	114.3 (6)
O1—Cu1—O3	98.7 (2)	C7—C6—C5	123.8 (6)
N1—Cu1—O3	99.9 (3)	C8—C7—C6	118.6 (7)
N2—Cu1—O3	87.6 (2)	C8—C7—H7	120.7
O1—Cu1—Cl1	90.87 (16)	C6—C7—H7	120.7
N1—Cu1—Cl1	95.37 (19)	C9—C8—C7	119.8 (7)
N2—Cu1—Cl1	174.95 (19)	C9—C8—H8	120.1
O3—Cu1—Cl1	92.75 (17)	C7—C8—H8	120.1
C5—N1—C1	116.6 (7)	C8—C9—C10	119.0 (7)
C5—N1—Cu1	116.3 (5)	C8—C9—H9	120.5
C1—N1—Cu1	127.1 (5)	C10—C9—H9	120.5
C10—N2—C6	119.4 (6)	N2—C10—C9	121.4 (7)
C10—N2—Cu1	124.9 (5)	N2—C10—H10	119.3
C6—N2—Cu1	115.8 (5)	C9—C10—H10	119.3
C11—O1—Cu1	111.9 (5)	O2—C11—O1	123.9 (7)
Cu1—O3—H3A	126.3	O2—C11—C12	120.2 (6)
Cu1—O3—H3B	122.4	O1—C11—C12	115.8 (7)
H3A—O3—H3B	108.0	C13—C12—C11	115.9 (6)
H4A—O4—H4B	108.7	C13—C12—H12A	108.3
C2—C1—N1	124.1 (8)	C11—C12—H12A	108.3
C2—C1—H1	118.0	C13—C12—H12B	108.3
N1—C1—H1	118.0	C11—C12—H12B	108.3
C3—C2—C1	117.1 (8)	H12A—C12—H12B	107.4
C3—C2—H2	121.5	C14—C13—C15	118.9 (7)
C1—C2—H2	121.5	C14—C13—C12	121.0 (7)
C2—C3—C4	121.2 (8)	C15—C13—C12	120.1 (6)
C2—C3—H3	119.4	C13—C14—C15ⁱ	120.6 (7)
C4—C3—H3	119.4	C13—C14—H14	119.7
C3—C4—C5	118.4 (7)	C15ⁱ—C14—H14	119.7
C3—C4—H4	120.8	C13—C15—C14ⁱ	120.6 (7)
C5—C4—H4	120.8	C13—C15—H15	119.7
N1—C5—C4	122.5 (7)	C14ⁱ—C15—H15	119.7
N1—C5—C6	114.0 (6)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱⁱ	0.85	2.00	2.822 (8)	164
O3—H3B···O4ⁱⁱⁱ	0.85	1.94	2.769 (8)	164
O4—H4A···O1	0.85	2.06	2.900 (8)	169
O4—H4B···Cl1ⁱⁱⁱ	0.85	2.44	3.276 (7)	169

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₀H₈O₄)Cl₂(C₁₀H₈N₂)₂(H₂O)₂]·2H₂O
M_r	774.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.713 (4), 6.954 (2), 19.585 (7)
β (°)	100.507 (5)
V (Å³)	1568.6 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.58
Crystal size (mm)	0.41 × 0.39 × 0.37

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.563, 0.592
No. of measured, independent and observed [I > 2σ(I)] reflections	7958, 3011, 2394
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.177, 1.06
No. of reflections	3011
No. of parameters	209
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0067P)² + 24.0162P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.79

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱ	0.85	2.00	2.822 (8)	164
O3—H3B···O4ⁱⁱ	0.85	1.94	2.769 (8)	164
O4—H4A···O1	0.85	2.06	2.900 (8)	169
O4—H4B···Cl1ⁱⁱ	0.85	2.44	3.276 (7)	169

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

References

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