Aqua­(pyridine-3-carb­oxy­lic acid-κN)(pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)copper(II) monohydrate

Chen, T.T.; Shang, Y.F.; Xi, X.; Zhang, Y.H.; Wang, N.P.

doi:10.1107/S160053681101926X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m809

doi:10.1107/S160053681101926X

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Aqua(pyridine-3-carboxylic acid-κN)(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)copper(II) monohydrate

Ting Ting Chen,^a Yan Fang Shang,^a Xia Xi,^a Yue Hua Zhang ^a and Nan Ping Wang ^a ^*

^aSchool of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, People's Republic of China
^*Correspondence e-mail: nanpingwang2010@yahoo.com.cn

(Received 5 April 2011; accepted 20 May 2011; online 28 May 2011)

In the title Cu^II complex, [Cu(C₇H₃NO₄)(C₆H₅NO₂)(H₂O)]·H₂O, the environment of the Cu²⁺ ion is a distorted square pyramid with the axial site occupied by the O atom from the coordinated water molecule and the square base formed by two O and two N atoms from the tridentate anion and the neutral monodentate pyridine-3-carboxylic acid ligand. O—H⋯O hydrogen bonds, as well as π–π interactions [centroid–centroid distance = 3.945 (3) Å] contribute to the stabilization of this structure.

Related literature

For the use of transition-metal–carboxylate systems in supramolecular chemistry and functional materials, see: MacDonald et al. (2000 ); Siddiqui et al. (2008 ); Custelcean & Gorbunova (2005 ). For a description of the geometry of complexes with five-coordinate metal atoms, see: Addison et al. (1984 ).

Experimental

Crystal data

[Cu(C₇H₃NO₄)(C₆H₅NO₂)(H₂O)]·H₂O
M_r = 387.79
Triclinic, $[P \overline 1]$
a = 7.3241 (12) Å
b = 9.5290 (16) Å
c = 11.1895 (18) Å
α = 107.471 (3)°
β = 92.822 (3)°
γ = 101.547 (3)°
V = 724.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.56 mm⁻¹
T = 293 K
0.34 × 0.28 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.612, T_max = 0.674
3704 measured reflections
2544 independent reflections
2036 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.089
S = 1.01
2544 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O1Wⁱ	0.85	1.87	2.715 (4)	175
O5—H5A⋯O7ⁱ	0.85	2.08	2.888 (4)	158
O6—H6⋯O4ⁱⁱ	0.82	1.79	2.586 (4)	164
O1W—H1WC⋯O3ⁱⁱⁱ	0.85	2.14	2.983 (4)	172
O1W—H1WD⋯O2	0.85	1.95	2.775 (4)	163
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) x, y+1, z+1; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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/S160053681101926X/yk2006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101926X/yk2006Isup2.hkl

checkCIF report

Comment top

In recent years, the chemistry of transition metal carboxylate systems is of great interest because of their extensive usage in supramolecular chemistry and functional materials (Custelcean & Gorbunova, 2005; MacDonald, et al., 2000; Siddiqui, et al., 2008). Here, we report a new Cu^IIcomplex with pyridine-2,6-dicarboxylic acid and pyridine-3-carboxylic acid.

In this complex, the Cu²⁺ ion is coordinated by one oxygen atom from water molecule, two oxygen atoms from the dianion of pyridine-2,6-dicarboxylic acid, and two nitrogen atoms from pyridine-2,6-dicarboxylate and pyridine-3-carboxylic acid, respectively (Fig. 1). Thus, the coordination environment of Cu²⁺ ion is a distorted square pyramid, as indicated by τ value of 0.06 (Addison, et al., 1984). The asymmetric units are linked into three-dimensional structure through C—H···O and O—H···O hydrogen bonds and π-π interactions between the neighbouring pyridine rings with centroid–centroid distance of 3.945 (3) Å (Fig. 2).

Related literature top

For the use of transition-metal–carboxylate systems in supramolecular chemistry and functional materials, see: MacDonald et al. (2000); Siddiqui et al. (2008); Custelcean & Gorbunova (2005). For a description of the geometry of complexes with five-coordinate metal atoms, see: Addison et al. (1984).

Experimental top

A mixture of Cu(CH₃COO)₂^.H₂O (0.5 mmol), pyridine-2,6-dicarboxylic acid (0.5 mmol), pyridine-3-carboxylic acid (0.5 mmol) in H₂O (4 ml) and CH₃OH (4 ml) was adjusted to pH ca 7.5 by triethylamine, sealed in a Teflon lined stainless steel container and heated at 140 °C for 3 days. After the sample was cooled to room temperature, blue crystals were collected with a yield of 30%.

Computing details top

Data collection: APEX2(Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SHELXTL (Sheldrick, 2008); 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 molecular structure of the title complex, with atomic labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The three-dimensional packing diagram of title compound, showing O—H···O and C—H···O hydrogen-bonds (dashed lines) and π–π interactions.

Aqua(pyridine-3-carboxylic acid-κN)(pyridine-2,6-dicarboxylato- κ³O²,N,O⁶)copper(II) monohydrate top

Crystal data top

[Cu(C₇H₃NO₄)(C₆H₅NO₂)(H₂O)]·H₂O	Z = 2
M_r = 387.79	F(000) = 394
Triclinic, P1	D_x = 1.777 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3241 (12) Å	Cell parameters from 3246 reflections
b = 9.5290 (16) Å	θ = 1.9–28.0°
c = 11.1895 (18) Å	µ = 1.56 mm⁻¹
α = 107.471 (3)°	T = 293 K
β = 92.822 (3)°	Block, blue
γ = 101.547 (3)°	0.34 × 0.28 × 0.24 mm
V = 724.8 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	2544 independent reflections
Radiation source: fine-focus sealed tube	2036 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
T_min = 0.612, T_max = 0.674	k = −11→7
3704 measured reflections	l = −13→12

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0156P)² + 0.0P] where P = (F_o² + 2F_c²)/3
2544 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Cu(C₇H₃NO₄)(C₆H₅NO₂)(H₂O)]·H₂O	γ = 101.547 (3)°
M_r = 387.79	V = 724.8 (2) Å³
Triclinic, P1	Z = 2
a = 7.3241 (12) Å	Mo Kα radiation
b = 9.5290 (16) Å	µ = 1.56 mm⁻¹
c = 11.1895 (18) Å	T = 293 K
α = 107.471 (3)°	0.34 × 0.28 × 0.24 mm
β = 92.822 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2544 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2036 reflections with I > 2σ(I)
T_min = 0.612, T_max = 0.674	R_int = 0.058
3704 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.01	Δρ_max = 0.61 e Å⁻³
2544 reflections	Δρ_min = −0.38 e Å⁻³
218 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 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	0.72746 (7)	0.75885 (6)	0.84260 (4)	0.03334 (18)
C1	0.6201 (6)	0.9587 (5)	0.7304 (4)	0.0314 (10)
C2	0.6438 (5)	0.8236 (4)	0.6230 (3)	0.0285 (9)
C3	0.6152 (6)	0.7997 (5)	0.4943 (4)	0.0358 (10)
H3	0.5722	0.8684	0.4626	0.043*
C4	0.6533 (6)	0.6692 (5)	0.4152 (4)	0.0354 (10)
H4	0.6343	0.6497	0.3284	0.043*
C5	0.7184 (5)	0.5677 (5)	0.4608 (3)	0.0340 (10)
H5	0.7459	0.4815	0.4064	0.041*
C6	0.7420 (5)	0.5976 (4)	0.5907 (3)	0.0289 (9)
C7	0.8072 (5)	0.5053 (5)	0.6655 (4)	0.0304 (10)
C8	0.9050 (6)	0.7252 (5)	1.0648 (4)	0.0397 (11)
H8	0.9215	0.6365	1.0073	0.048*
C9	0.9646 (6)	0.7553 (5)	1.1898 (4)	0.0374 (11)
H9	1.0196	0.6885	1.2168	0.045*
C10	0.9409 (5)	0.8866 (5)	1.2737 (4)	0.0353 (10)
H10	0.9783	0.9095	1.3593	0.042*
C11	0.8617 (5)	0.9847 (4)	1.2313 (3)	0.0275 (9)
C12	0.8029 (5)	0.9449 (4)	1.1039 (3)	0.0316 (10)
H12	0.7465	1.0095	1.0748	0.038*
C13	0.8343 (6)	1.1300 (5)	1.3159 (4)	0.0326 (10)
N1	0.7036 (4)	0.7233 (4)	0.6650 (3)	0.0286 (8)
N2	0.8244 (5)	0.8170 (4)	1.0215 (3)	0.0328 (8)
O1	0.6624 (4)	0.9519 (3)	0.8403 (2)	0.0372 (7)
O2	0.5679 (4)	1.0631 (3)	0.7065 (2)	0.0413 (8)
O3	0.8087 (4)	0.5614 (3)	0.7853 (2)	0.0376 (7)
O4	0.8507 (4)	0.3867 (3)	0.6120 (2)	0.0447 (8)
O5	0.4365 (4)	0.6488 (3)	0.8620 (2)	0.0461 (8)
H5B	0.4206	0.6493	0.9369	0.069*
H5A	0.3623	0.6970	0.8400	0.069*
O6	0.8709 (5)	1.1433 (3)	1.4365 (2)	0.0436 (8)
H6	0.8607	1.2267	1.4806	0.065*
O7	0.7889 (4)	1.2257 (3)	1.2796 (3)	0.0456 (8)
O1W	0.5969 (5)	1.3367 (3)	0.8942 (3)	0.0705 (11)
H1WC	0.6522	1.4074	0.8683	0.106*
H1WD	0.6098	1.2529	0.8447	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0503 (3)	0.0311 (3)	0.0194 (3)	0.0134 (3)	0.0010 (2)	0.0071 (2)
C1	0.034 (2)	0.030 (2)	0.031 (2)	0.006 (2)	0.0038 (18)	0.012 (2)
C2	0.032 (2)	0.033 (2)	0.024 (2)	0.010 (2)	0.0030 (17)	0.0127 (19)
C3	0.040 (3)	0.040 (3)	0.032 (2)	0.009 (2)	0.0003 (19)	0.019 (2)
C4	0.043 (3)	0.043 (3)	0.019 (2)	0.005 (2)	0.0024 (18)	0.012 (2)
C5	0.038 (2)	0.034 (3)	0.026 (2)	0.005 (2)	0.0084 (18)	0.006 (2)
C6	0.029 (2)	0.030 (2)	0.025 (2)	0.006 (2)	0.0018 (17)	0.0070 (19)
C7	0.033 (2)	0.029 (2)	0.028 (2)	0.008 (2)	0.0020 (18)	0.007 (2)
C8	0.052 (3)	0.033 (3)	0.034 (2)	0.016 (2)	0.001 (2)	0.006 (2)
C9	0.050 (3)	0.039 (3)	0.027 (2)	0.016 (2)	−0.0017 (19)	0.013 (2)
C10	0.038 (3)	0.044 (3)	0.021 (2)	0.007 (2)	−0.0010 (18)	0.009 (2)
C11	0.031 (2)	0.029 (2)	0.021 (2)	0.0022 (19)	0.0013 (16)	0.0084 (18)
C12	0.041 (3)	0.027 (2)	0.026 (2)	0.009 (2)	0.0022 (18)	0.0079 (19)
C13	0.032 (2)	0.034 (3)	0.026 (2)	0.003 (2)	−0.0011 (18)	0.004 (2)
N1	0.035 (2)	0.030 (2)	0.0204 (17)	0.0055 (17)	0.0008 (14)	0.0087 (15)
N2	0.041 (2)	0.036 (2)	0.0220 (18)	0.0128 (18)	0.0016 (15)	0.0084 (16)
O1	0.058 (2)	0.0322 (17)	0.0246 (15)	0.0160 (15)	0.0012 (13)	0.0098 (13)
O2	0.056 (2)	0.0345 (18)	0.0377 (17)	0.0172 (16)	−0.0006 (14)	0.0149 (14)
O3	0.062 (2)	0.0345 (17)	0.0184 (15)	0.0219 (15)	0.0017 (13)	0.0056 (13)
O4	0.071 (2)	0.0382 (18)	0.0262 (16)	0.0273 (17)	0.0013 (14)	0.0037 (14)
O5	0.051 (2)	0.057 (2)	0.0354 (17)	0.0119 (17)	0.0056 (14)	0.0217 (16)
O6	0.067 (2)	0.0390 (19)	0.0219 (15)	0.0192 (18)	0.0012 (14)	0.0012 (14)
O7	0.066 (2)	0.0359 (19)	0.0338 (17)	0.0190 (17)	−0.0024 (15)	0.0061 (15)
O1W	0.126 (3)	0.044 (2)	0.044 (2)	0.018 (2)	0.033 (2)	0.0157 (17)

Geometric parameters (Å, º) top

Cu1—N1	1.906 (3)	C7—O3	1.284 (4)
Cu1—N2	1.963 (3)	C8—N2	1.335 (5)
Cu1—O1	1.998 (3)	C8—C9	1.370 (5)
Cu1—O3	2.017 (3)	C8—H8	0.9300
Cu1—O5	2.231 (3)	C9—C10	1.370 (5)
C1—O2	1.229 (5)	C9—H9	0.9300
C1—O1	1.277 (4)	C10—C11	1.374 (5)
C1—C2	1.520 (5)	C10—H10	0.9300
C2—N1	1.321 (5)	C11—C12	1.383 (5)
C2—C3	1.387 (5)	C11—C13	1.482 (5)
C3—C4	1.381 (5)	C12—N2	1.333 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.371 (5)	C13—O7	1.198 (5)
C4—H4	0.9300	C13—O6	1.327 (4)
C5—C6	1.389 (5)	O5—H5B	0.8500
C5—H5	0.9300	O5—H5A	0.8501
C6—N1	1.329 (4)	O6—H6	0.8200
C6—C7	1.507 (5)	O1W—H1WC	0.8500
C7—O4	1.222 (5)	O1W—H1WD	0.8499

N1—Cu1—N2	164.24 (13)	N2—C8—C9	123.2 (4)
N1—Cu1—O1	81.06 (12)	N2—C8—H8	118.4
N2—Cu1—O1	99.27 (12)	C9—C8—H8	118.4
N1—Cu1—O3	80.30 (12)	C10—C9—C8	118.1 (4)
N2—Cu1—O3	97.28 (12)	C10—C9—H9	121.0
O1—Cu1—O3	160.68 (10)	C8—C9—H9	121.0
N1—Cu1—O5	99.42 (11)	C9—C10—C11	120.0 (4)
N2—Cu1—O5	96.26 (12)	C9—C10—H10	120.0
O1—Cu1—O5	94.65 (11)	C11—C10—H10	120.0
O3—Cu1—O5	93.36 (11)	C10—C11—C12	118.4 (4)
O2—C1—O1	126.0 (4)	C10—C11—C13	123.2 (3)
O2—C1—C2	119.6 (3)	C12—C11—C13	118.4 (4)
O1—C1—C2	114.3 (4)	N2—C12—C11	122.1 (4)
N1—C2—C3	120.0 (4)	N2—C12—H12	118.9
N1—C2—C1	111.8 (3)	C11—C12—H12	118.9
C3—C2—C1	128.2 (4)	O7—C13—O6	124.0 (4)
C4—C3—C2	117.1 (4)	O7—C13—C11	124.1 (4)
C4—C3—H3	121.5	O6—C13—C11	111.9 (4)
C2—C3—H3	121.5	C2—N1—C6	123.9 (3)
C5—C4—C3	122.0 (4)	C2—N1—Cu1	117.6 (3)
C5—C4—H4	119.0	C6—N1—Cu1	118.5 (3)
C3—C4—H4	119.0	C12—N2—C8	118.2 (3)
C4—C5—C6	118.0 (4)	C12—N2—Cu1	121.1 (3)
C4—C5—H5	121.0	C8—N2—Cu1	120.6 (3)
C6—C5—H5	121.0	C1—O1—Cu1	114.7 (3)
N1—C6—C5	119.0 (4)	C7—O3—Cu1	115.1 (2)
N1—C6—C7	111.8 (3)	Cu1—O5—H5B	113.4
C5—C6—C7	129.2 (4)	Cu1—O5—H5A	107.7
O4—C7—O3	125.2 (4)	H5B—O5—H5A	108.0
O4—C7—C6	120.6 (3)	C13—O6—H6	109.5
O3—C7—C6	114.3 (3)	H1WC—O1W—H1WD	108.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O1Wⁱ	0.85	1.87	2.715 (4)	175
O5—H5A···O7ⁱ	0.85	2.08	2.888 (4)	158
O6—H6···O4ⁱⁱ	0.82	1.79	2.586 (4)	164
O1W—H1WC···O3ⁱⁱⁱ	0.85	2.14	2.983 (4)	172
O1W—H1WD···O2	0.85	1.95	2.775 (4)	163

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

Experimental details

Crystal data
Chemical formula	[Cu(C₇H₃NO₄)(C₆H₅NO₂)(H₂O)]·H₂O
M_r	387.79
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.3241 (12), 9.5290 (16), 11.1895 (18)
α, β, γ (°)	107.471 (3), 92.822 (3), 101.547 (3)
V (Å³)	724.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.56
Crystal size (mm)	0.34 × 0.28 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.612, 0.674
No. of measured, independent and observed [I > 2σ(I)] reflections	3704, 2544, 2036
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.089, 1.01
No. of reflections	2544
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.38

Computer programs: APEX2(Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O1Wⁱ	0.85	1.87	2.715 (4)	175.4
O5—H5A···O7ⁱ	0.85	2.08	2.888 (4)	158.1
O6—H6···O4ⁱⁱ	0.82	1.79	2.586 (4)	163.5
O1W—H1WC···O3ⁱⁱⁱ	0.85	2.14	2.983 (4)	171.7
O1W—H1WD···O2	0.85	1.95	2.775 (4)	162.7

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

Acknowledgements

We are grateful for financial support from the Science and Technology Bureau of Nantong (grant No. K2009041).

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