Diazido­bis(propane-1,3-diamine)copper(II)

Khan, I.U.; Ejaz; Şahin, O.; Büyükgüngör, O.

doi:10.1107/S1600536810010184

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages m434-m435

doi:10.1107/S1600536810010184

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Diazidobis(propane-1,3-diamine)copper(II)

Islam Ullah Khan,^a ^* Ejaz,^a Onur Şahin ^b ^* and Orhan Büyükgüngör ^b

^aMaterials Chemistry Laboratry, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey
^*Correspondence e-mail: iuklodhi@yahoo.com, onurs@omu.edu.tr

(Received 4 March 2010; accepted 18 March 2010; online 24 March 2010)

In the title complex, [Cu(N₃)₂(C₃H₁₀N₂)₂], the Cu^II ion resides on a centre of symmetry and is in a Jahn–Teller distorted octahedral coordination environment comprising two N atoms from azide anions in axial positions and four N atoms from propane-1,3-diamine (tn) ligands in equatorial positions. Intermolecular N—H⋯N hydrogen bonds produce R₂¹(6), R₂²(8), R₂²(12) and R₄²(8) rings, generating a two-dimensional layer.

Related literature

For related structures, see: Escuer et al. (1997 ); Gu et al. (2007 ); Mondal & Mukherjee (2008 ); Monfort et al. (2000 ); Shen et al. (2000 ); Sundberg & Sillanpaa (1993 ); Sundberg & Uggla (1997 ); Sundberg et al. (2001 ); Zhang et al. (2009 ); Luo et al. (2004 ); Triki et al. (2005 ). For graph-set motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

[Cu(N₃)₂(C₃H₁₀N₂)₂]
M_r = 295.86
Triclinic, $[P \overline 1]$
a = 6.6869 (4) Å
b = 6.7743 (4) Å
c = 8.2445 (8) Å
α = 93.296 (3)°
β = 98.306 (3)°
γ = 119.453 (2)°
V = 318.19 (4) Å³
Z = 1
Mo Kα radiation
μ = 1.72 mm⁻¹
T = 296 K
0.27 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII diffractometer
5360 measured reflections
1497 independent reflections
1467 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.077
S = 1.01
1497 reflections
95 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N1—Cu1	2.0333 (13)
N2—Cu1	2.0302 (13)
N3—N5	1.169 (2)
N4—N5	1.168 (2)
N4—Cu1	2.6740 (17)

N5—N4—Cu1	99.05 (12)
N4—N5—N3	179.8 (2)
N2—Cu1—N1	87.19 (5)
N2—Cu1—N4	83.92 (5)
N1—Cu1—N4	87.19 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3ⁱ	0.84 (1)	2.12 (2)	2.962 (2)	173 (2)
N1—H2⋯N4ⁱⁱ	0.85 (2)	2.66 (2)	3.511 (2)	173 (2)
N2—H3⋯N3ⁱⁱ	0.83 (2)	2.44 (2)	3.220 (2)	158 (2)
N2—H4⋯N3ⁱⁱⁱ	0.80 (2)	2.31 (2)	3.078 (2)	162 (2)
Symmetry codes: (i) -x+3, -y, -z; (ii) -x+3, -y+1, -z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010184/om2325sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010184/om2325Isup2.hkl

checkCIF report

Comment top

Recently, metal azide complexes have attracted great attention (Mondal & Mukherjee, 2008; Gu et al., 2007). The azide anion has rich coordination modes (Shen et al., 2000), and many metal-azide complexes have been reported (Monfort et al., 2000). In most of the compounds reported to date, the co-ligands are neutral organic ligands, while charged ligands are very scarce (Escuer et al., 1997). The 1,3-diaminopropane (tn) ligand behaves as a strong chelatator in its metal complexes due to the formation of a stable six-membered ring. At the same time, it is a good H-bond donor due to the existence of amino groups (Sundberg et al., 2001). Previously, the polymorphic dinuclear compound featuring both bridging and terminal azido groups was reported (Luo et al., 2004; Triki et al., 2005). Herein, we report the synthesis and structure of the mononuclear complex with only terminal azido ligands.

The molecular structure and atom-labelling scheme are shown in Fig. 1. The Cu^II atom is located on a center of symmetry and is coordinated by four N atoms from two tn ligands and two N atoms from two azide anions. The geometry around the Cu^II ion (Table 1) is that of a distorted octahedron, the equatorial plane of which (N1/N2/N1ⁱ/N2ⁱ) is formed by four amino N atoms [symmetry code: (i) 2-x, -y, -z]. The axial positions in the octahedron are occupied by two N atoms (N4 and N4ⁱ). The Cu1—N4 distance is longer than the corresponding distances in related structures (Luo et al., 2004; Triki et al., 2005). This elongation can be attributed to the static Jahn-Teller effect. The tn ligand shows chelating coordination behavior and displays a chair conformation in the equatorial direction. This kind of coordination mode was also found in the similar complexes (Sundberg et al., 2001; Sundberg & Sillanpaa, 1993; Sundberg & Uggla, 1997). The Cu1—N1 and Cu1—N2 bond lengths are very similar to those in the previously reported Bis(4-aminobenzenesulfonato-κO)bis(propane-1,3-diamine-κ²N,N')copper(II) dihydrate (Zhang et al., 2009).

Amino atom N2 in the molecule at (x, y, z) acts as a hydrogen-bond donor, via H3, to atom N3ⁱⁱ so forming a C(6) (Bernstein et al., 1995) chain running parallel to the [110] direction. Amino atom N2 in the molecule at (x, y, z) acts as a hydrogen-bond donor, via H4, to atom N3ⁱⁱⁱ so forming a C(6) chain running parallel to the [-100] direction. Similarly, amino atom N1 in the molecule at (x, y, z) acts as a hydrogen-bond donor, via H1, to atom N3ⁱ so forming a C(6) chain running parallel to the [100] direction. Amino atom N1 in the molecule at (x, y, z) acts as a hydrogen-bond donor, via H2, to atom N4ⁱⁱ so forming a C(4) chain running parallel to the [110] direction. The combination of C(4) and C(6) chains produce R₂¹(6), R₂²(8), R₂²(12) and R₄²(8) rings (Fig. 2).

Related literature top

For related structures, see: Escuer et al. (1997); Gu et al. (2007); Mondal & Mukherjee (2008); Monfort et al. (2000); Shen et al. (2000); Sundberg & Sillanpaa (1993); Sundberg & Uggla (1997); Sundberg et al. (2001); Zhang et al. (2009); Luo et al. (2004); Triki et al. (2005). For graph-set motifs, see: Bernstein et al. (1995).

Experimental top

Copper(II) sulphate (0.16 g, 1.0 mmol) was dissolved in methanol (20 ml). Sodium azide (0.134 g, 2.0 mmol) and 1,3-diaminopropane(0.148 g, 2.0 mmol) were added and the mixture refluxed for 3 hours. A blue solution formed, which was filtered. After a few days, blue blocks were obtained from the methanol filtrate.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of one molecule showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry code: (i) 2-x, -y, -z.]
	Fig. 2. Part of the crystal structure showing the formation of R₂¹(6), R₂²(8), R₂²(12) and R₄²(8) rings. H atoms not involved in these interactions have been omitted for clarity. (Symmetry codes as in Table 2).

Diazidobis(propane-1,3-diamine)copper(II) top

Crystal data top

[Cu(N₃)₂(C₃H₁₀N₂)₂]	Z = 1
M_r = 295.86	F(000) = 155
Triclinic, P1	D_x = 1.544 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6869 (4) Å	Cell parameters from 4650 reflections
b = 6.7743 (4) Å	θ = 3.5–28.6°
c = 8.2445 (8) Å	µ = 1.72 mm⁻¹
α = 93.296 (3)°	T = 296 K
β = 98.306 (3)°	Blocks, blue
γ = 119.453 (2)°	0.27 × 0.25 × 0.22 mm
V = 318.19 (4) Å³

Data collection top

Bruker Kappa APEXII diffractometer	1467 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 28.0°, θ_min = 2.5°
ϕ and ω scans	h = −8→5
5360 measured reflections	k = −8→8
1497 independent reflections	l = −10→10

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0676P)² + 0.0082P] where P = (F_o² + 2F_c²)/3
1497 reflections	(Δ/σ)_max < 0.001
95 parameters	Δρ_max = 0.42 e Å⁻³
4 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Cu(N₃)₂(C₃H₁₀N₂)₂]	γ = 119.453 (2)°
M_r = 295.86	V = 318.19 (4) Å³
Triclinic, P1	Z = 1
a = 6.6869 (4) Å	Mo Kα radiation
b = 6.7743 (4) Å	µ = 1.72 mm⁻¹
c = 8.2445 (8) Å	T = 296 K
α = 93.296 (3)°	0.27 × 0.25 × 0.22 mm
β = 98.306 (3)°

Data collection top

Bruker Kappa APEXII diffractometer	1467 reflections with I > 2σ(I)
5360 measured reflections	R_int = 0.023
1497 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	4 restraints
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.42 e Å⁻³
1497 reflections	Δρ_min = −0.44 e Å⁻³
95 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	1.2523 (3)	0.1281 (3)	0.3530 (2)	0.0388 (4)
H1A	1.3929	0.1612	0.4300	0.047*
H1B	1.1251	−0.0175	0.3700	0.047*
C2	1.1953 (3)	0.3138 (3)	0.3892 (2)	0.0401 (4)
H2A	1.3207	0.4574	0.3679	0.048*
H2B	1.1916	0.3312	0.5062	0.048*
C3	0.9655 (3)	0.2714 (3)	0.2899 (2)	0.0400 (4)
H3A	0.8381	0.1311	0.3136	0.048*
H3B	0.9412	0.3964	0.3233	0.048*
N1	1.2889 (2)	0.1090 (2)	0.18062 (17)	0.0313 (3)
H1	1.338 (3)	0.017 (3)	0.173 (2)	0.029 (5)*
H2	1.398 (3)	0.241 (3)	0.169 (3)	0.034 (5)*
N2	0.9619 (2)	0.2524 (2)	0.10959 (17)	0.0317 (3)
H3	1.078 (3)	0.368 (3)	0.093 (3)	0.037 (5)*
H4	0.855 (3)	0.261 (4)	0.060 (3)	0.040 (6)*
N3	1.5787 (3)	0.2474 (3)	−0.1503 (2)	0.0483 (4)
N4	1.2752 (3)	0.3278 (3)	−0.1626 (2)	0.0446 (3)
N5	1.4271 (2)	0.2879 (2)	−0.15632 (16)	0.0310 (3)
Cu1	1.0000	0.0000	0.0000	0.02769 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0421 (9)	0.0354 (8)	0.0248 (8)	0.0114 (7)	−0.0028 (6)	0.0058 (6)
C2	0.0409 (9)	0.0375 (8)	0.0246 (7)	0.0085 (7)	0.0031 (6)	−0.0030 (6)
C3	0.0374 (8)	0.0407 (9)	0.0331 (8)	0.0141 (7)	0.0078 (7)	−0.0065 (7)
N1	0.0284 (6)	0.0309 (6)	0.0293 (6)	0.0132 (5)	−0.0013 (5)	0.0012 (5)
N2	0.0278 (6)	0.0320 (7)	0.0304 (7)	0.0136 (5)	−0.0001 (5)	−0.0004 (5)
N3	0.0379 (8)	0.0398 (8)	0.0659 (11)	0.0211 (7)	0.0029 (7)	0.0040 (7)
N4	0.0365 (7)	0.0575 (9)	0.0397 (8)	0.0255 (7)	0.0029 (6)	0.0027 (7)
N5	0.0288 (6)	0.0254 (6)	0.0294 (6)	0.0069 (5)	0.0043 (5)	0.0056 (5)
Cu1	0.02519 (16)	0.03367 (17)	0.02129 (17)	0.01466 (12)	−0.00046 (10)	−0.00212 (10)

Geometric parameters (Å, º) top

C1—N1	1.486 (2)	N1—H1	0.843 (14)
C1—C2	1.509 (3)	N1—H2	0.852 (15)
C1—H1A	0.9700	N2—Cu1	2.0302 (13)
C1—H1B	0.9700	N2—H3	0.826 (16)
C2—C3	1.513 (2)	N2—H4	0.801 (15)
C2—H2A	0.9700	N3—N5	1.169 (2)
C2—H2B	0.9700	N4—N5	1.168 (2)
C3—N2	1.480 (2)	N4—Cu1	2.6740 (17)
C3—H3A	0.9700	Cu1—N2ⁱ	2.0302 (13)
C3—H3B	0.9700	Cu1—N1ⁱ	2.0333 (13)
N1—Cu1	2.0333 (13)

N1—C1—C2	111.99 (13)	C1—N1—H2	106.5 (15)
N1—C1—H1A	109.2	Cu1—N1—H2	110.7 (14)
C2—C1—H1A	109.2	H1—N1—H2	108.1 (19)
N1—C1—H1B	109.2	C3—N2—Cu1	118.90 (11)
C2—C1—H1B	109.2	C3—N2—H3	108.0 (15)
H1A—C1—H1B	107.9	Cu1—N2—H3	101.3 (15)
C1—C2—C3	114.90 (15)	C3—N2—H4	110.7 (17)
C1—C2—H2A	108.5	Cu1—N2—H4	113.0 (17)
C3—C2—H2A	108.5	H3—N2—H4	103 (2)
C1—C2—H2B	108.5	N5—N4—Cu1	99.05 (12)
C3—C2—H2B	108.5	N4—N5—N3	179.8 (2)
H2A—C2—H2B	107.5	N2—Cu1—N2ⁱ	180.00 (7)
N2—C3—C2	111.68 (13)	N2—Cu1—N1	87.19 (5)
N2—C3—H3A	109.3	N2ⁱ—Cu1—N1	92.81 (5)
C2—C3—H3A	109.3	N2—Cu1—N1ⁱ	92.81 (5)
N2—C3—H3B	109.3	N2ⁱ—Cu1—N1ⁱ	87.19 (5)
C2—C3—H3B	109.3	N1—Cu1—N1ⁱ	180.00 (6)
H3A—C3—H3B	107.9	N2—Cu1—N4	83.92 (5)
C1—N1—Cu1	115.28 (10)	N2ⁱ—Cu1—N4	96.08 (5)
C1—N1—H1	107.0 (13)	N1—Cu1—N4	87.19 (5)
Cu1—N1—H1	109.1 (14)	N1ⁱ—Cu1—N4	92.81 (5)

N1—C1—C2—C3	64.96 (19)	C1—N1—Cu1—N2	52.35 (11)
C1—C2—C3—N2	−60.6 (2)	C1—N1—Cu1—N2ⁱ	−127.65 (11)
C2—C1—N1—Cu1	−66.39 (15)	C1—N1—Cu1—N4	136.40 (11)
C2—C3—N2—Cu1	60.49 (17)	N5—N4—Cu1—N2	137.75 (12)
C3—N2—Cu1—N1	−50.92 (12)	N5—N4—Cu1—N2ⁱ	−42.25 (12)
C3—N2—Cu1—N1ⁱ	129.08 (12)	N5—N4—Cu1—N1	50.28 (12)
C3—N2—Cu1—N4	−138.39 (12)	N5—N4—Cu1—N1ⁱ	−129.72 (12)

Symmetry code: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱⁱ	0.84 (1)	2.12 (2)	2.962 (2)	173 (2)
N1—H2···N4ⁱⁱⁱ	0.85 (2)	2.66 (2)	3.511 (2)	173 (2)
N2—H3···N3ⁱⁱⁱ	0.83 (2)	2.44 (2)	3.220 (2)	158 (2)
N2—H4···N3^iv	0.80 (2)	2.31 (2)	3.078 (2)	162 (2)

Symmetry codes: (ii) −x+3, −y, −z; (iii) −x+3, −y+1, −z; (iv) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Cu(N₃)₂(C₃H₁₀N₂)₂]
M_r	295.86
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.6869 (4), 6.7743 (4), 8.2445 (8)
α, β, γ (°)	93.296 (3), 98.306 (3), 119.453 (2)
V (Å³)	318.19 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.72
Crystal size (mm)	0.27 × 0.25 × 0.22

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5360, 1497, 1467
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.077, 1.01
No. of reflections	1497
No. of parameters	95
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.44

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

N1—Cu1	2.0333 (13)	N4—N5	1.168 (2)
N2—Cu1	2.0302 (13)	N4—Cu1	2.6740 (17)
N3—N5	1.169 (2)

N5—N4—Cu1	99.05 (12)	N2—Cu1—N4	83.92 (5)
N4—N5—N3	179.8 (2)	N1—Cu1—N4	87.19 (5)
N2—Cu1—N1	87.19 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱ	0.843 (14)	2.123 (15)	2.962 (2)	173.3 (19)
N1—H2···N4ⁱⁱ	0.852 (15)	2.664 (16)	3.511 (2)	173.4 (19)
N2—H3···N3ⁱⁱ	0.826 (16)	2.438 (17)	3.220 (2)	158 (2)
N2—H4···N3ⁱⁱⁱ	0.801 (15)	2.305 (17)	3.078 (2)	162 (2)

Symmetry codes: (i) −x+3, −y, −z; (ii) −x+3, −y+1, −z; (iii) x−1, y, z.

Acknowledgements

IUK thanks the Higher Education Commission of Pakistan for its financial support under the project Strengthening of the Materials Chemistry Laboratory at GCUL.

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