Tetra­ethyl­ammonium tricarbonyl­chlorido­(pyrazine-2-carboxyl­ato-N1,O)rhenate(I)

Suthiram, J.; Mhlaba, K.; Zeevaart, J.R.; Visser, H.G.; Roodt, A.

doi:10.1107/S1600536809042160

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1395

https://doi.org/10.1107/S1600536809042160

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Tetraethylammonium tricarbonylchlorido(pyrazine-2-carboxylato-N¹,O)rhenate(I)

Janine Suthiram,^a Kanyisa Mhlaba,^a Jan Rijn Zeevaart,^a Hendrik G. Visser ^b ^* and Andreas Roodt ^b

^aRadiochemistry, South African Nuclear Energy Corporation Ltd. (Necsa), PO Box 582, Pretoria, 0001, South Africa, and ^bDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9300, South Africa
^*Correspondence e-mail: visserhg.sci@mail.uovs.ac.za

(Received 12 October 2009; accepted 14 October 2009; online 17 October 2009)

In the title complex, (C₈H₂₀N)[Re(C₅H₃N₂O₂)Cl(CO)₃], the Re^I atom is coordinated facially by three carbonyl groups; the bidentate pyrazinecarboxylato ligand and a chlorine atom complete the distorted octahedral coordination.

Related literature

For synthetic background, see: Alberto et al. (1996 ). For related structures, see: Schutte et al. (2008 ); Kemp (2006 ); Wang et al. (2003 ); Alvarez et al. (2007 ); Brasey et al. (2004 ); Mundwiler et al. (2004 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

(C₈H₂₀N)[Re(C₅H₃N₂O₂)Cl(CO)₃]
M_r = 559.02
Monoclinic, P 2₁ /c
a = 7.927 (5) Å
b = 22.278 (5) Å
c = 10.903 (5) Å
β = 90.506 (5)°
V = 1925.4 (16) Å³
Z = 4
Mo Kα radiation
μ = 6.48 mm⁻¹
T = 100 K
0.27 × 0.20 × 0.11 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.273, T_max = 0.539
32482 measured reflections
4781 independent reflections
4121 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.098
S = 1.18
4781 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 1.05 e Å⁻³
Δρ_min = −1.38 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809042160/pv2218sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042160/pv2218Isup2.hkl

checkCIF report

Comment top

The title complex, (I), forms a part of an ongoing investigation of the structural and kinetic behaviour of fac-Re(CO)₃ compounds (Schutte et al., 2008). It crystallized as an anionic Re^I compound and one tetraethylammonium counter ion in the asymmetric unit (Fig. 1). The Re—CO bond distances are well within the normal range (Allen et al., 1987). The small bite angle O4—Re1—N1 might be a reason for the slightly distorted octahedral geometry around the metal centre. There are no classical hydrogen bonds in the structure.

Related literature top

For synthetic background, see: Alberto et al. (1996). For related structures, see: Schutte et al. (2008); Kemp (2006); Wang et al. (2003); Alvarez et al. (2007); Brasey et al. (2004); Mundwiler et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

ReCl₃(CO)₃ (64.2 mg, 0.01 mmol) was suspended in 10 ml methanol. The solution was heated to reflux and 2-pyrazinecarboxylic acid (13.1 mg, 0.01 mmol) dissolved in ca 5 ml methanol was added whilst stirring. A bright yellow colour resulted on addition of the ligand to the metal. K₂CO₃ 7.1 mg (0.005 mmol) was added to the solution. The reaction solution was refluxed for 6 h after which the solvent volume was decreased on a rotovapor. The MeOH solution was layered with a minimal amount of diethyl ether and left to stand in a refrigerator. After a few days yellow crystals were formed.

Structure description top

For synthetic background, see: Alberto et al. (1996). For related structures, see: Schutte et al. (2008); Kemp (2006); Wang et al. (2003); Alvarez et al. (2007); Brasey et al. (2004); Mundwiler et al. (2004). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. A view of the title complex plotted with 50% probability displacement ellipsoids; hydrogen atoms have been omitted for clarity.

Tetraethylammonium tricarbonylchlorido(pyrazine-2-carboxylato-N¹,O)rhenate(I) top

Crystal data top

(C₈H₂₀N)[Re(C₅H₃N₂O₂)Cl(CO)₃]	F(000) = 1088
M_r = 559.02	D_x = 1.929 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9901 reflections
a = 7.927 (5) Å	θ = 2.7–28.3°
b = 22.278 (5) Å	µ = 6.48 mm⁻¹
c = 10.903 (5) Å	T = 100 K
β = 90.506 (5)°	Cuboid, yellow
V = 1925.4 (16) Å³	0.27 × 0.20 × 0.11 mm
Z = 4

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	4781 independent reflections
Radiation source: sealed tube	4121 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
phi and ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→9
T_min = 0.273, T_max = 0.539	k = −29→29
32482 measured reflections	l = −14→13

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.021	w = 1/[σ²(F_o²) + (0.0591P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.098	(Δ/σ)_max = 0.001
S = 1.18	Δρ_max = 1.05 e Å⁻³
4781 reflections	Δρ_min = −1.38 e Å⁻³
235 parameters

Crystal data top

(C₈H₂₀N)[Re(C₅H₃N₂O₂)Cl(CO)₃]	V = 1925.4 (16) Å³
M_r = 559.02	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.927 (5) Å	µ = 6.48 mm⁻¹
b = 22.278 (5) Å	T = 100 K
c = 10.903 (5) Å	0.27 × 0.20 × 0.11 mm
β = 90.506 (5)°

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	4781 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4121 reflections with I > 2σ(I)
T_min = 0.273, T_max = 0.539	R_int = 0.046
32482 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.18	Δρ_max = 1.05 e Å⁻³
4781 reflections	Δρ_min = −1.38 e Å⁻³
235 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.

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

	x	y	z	U_iso*/U_eq
Re1	0.30393 (2)	0.198197 (7)	0.407485 (15)	0.01064 (8)
Cl1	0.29768 (13)	0.09512 (5)	0.49378 (10)	0.0154 (2)
C5	0.3651 (5)	0.13259 (19)	0.1726 (4)	0.0117 (8)
O5	0.0904 (4)	0.10473 (15)	0.1121 (3)	0.0186 (7)
N3	0.1752 (4)	−0.07955 (16)	0.2734 (3)	0.0111 (7)
O4	0.1219 (4)	0.16145 (14)	0.2811 (3)	0.0143 (7)
N2	0.6136 (5)	0.10700 (19)	0.0608 (4)	0.0198 (9)
N1	0.4559 (5)	0.15900 (16)	0.2633 (3)	0.0132 (8)
C14	0.1057 (5)	−0.0443 (2)	0.1656 (4)	0.0146 (9)
H14B	0.1568	−0.0047	0.1666	0.018*
H14A	0.1403	−0.064	0.0906	0.018*
C4	0.1762 (5)	0.1323 (2)	0.1880 (4)	0.0131 (9)
C10	0.1294 (6)	−0.0471 (2)	0.3912 (4)	0.0169 (9)
H10A	0.1667	−0.0058	0.3849	0.02*
H10B	0.0075	−0.0467	0.3983	0.02*
C15	−0.0836 (6)	−0.0368 (2)	0.1619 (4)	0.0182 (10)
H15B	−0.1153	−0.0138	0.0909	0.027*
H15C	−0.1197	−0.0164	0.2345	0.027*
H15A	−0.1361	−0.0756	0.1578	0.027*
C12	0.3647 (5)	−0.0855 (2)	0.2602 (4)	0.0147 (9)
H12B	0.4069	−0.1106	0.3264	0.018*
H12A	0.3875	−0.1062	0.1838	0.018*
C17	0.1141 (6)	−0.1786 (2)	0.1620 (5)	0.0215 (10)
H17B	0.0637	−0.2173	0.1739	0.032*
H17A	0.231	−0.1835	0.1418	0.032*
H17C	0.0569	−0.1581	0.0962	0.032*
C1	0.4817 (6)	0.2209 (2)	0.5162 (4)	0.0160 (9)
C7	0.7019 (6)	0.1324 (2)	0.1527 (4)	0.0187 (10)
H7	0.819	0.1323	0.149	0.022*
C16	0.0997 (6)	−0.14213 (19)	0.2785 (4)	0.0139 (9)
H16A	0.1545	−0.1641	0.3445	0.017*
H16B	−0.0188	−0.1386	0.2988	0.017*
C13	0.4627 (6)	−0.0272 (2)	0.2612 (5)	0.0228 (11)
H13C	0.5808	−0.0355	0.2525	0.034*
H13B	0.4444	−0.0067	0.3374	0.034*
H13A	0.425	−0.0023	0.1945	0.034*
C8	0.6250 (6)	0.1586 (2)	0.2526 (4)	0.0167 (9)
H8	0.6913	0.1764	0.3134	0.02*
C6	0.4450 (6)	0.1077 (2)	0.0729 (4)	0.0169 (9)
H6	0.3791	0.0906	0.0111	0.02*
C11	0.2032 (6)	−0.0737 (2)	0.5073 (4)	0.0227 (11)
H11B	0.1677	−0.0504	0.5765	0.034*
H11A	0.3241	−0.0733	0.5028	0.034*
H11C	0.1646	−0.1143	0.5162	0.034*
C3	0.1409 (6)	0.2291 (2)	0.5218 (4)	0.0148 (9)
O2	0.3224 (4)	0.32482 (15)	0.2989 (3)	0.0206 (7)
O3	0.0411 (4)	0.24882 (16)	0.5855 (3)	0.0215 (7)
O1	0.5931 (4)	0.23294 (16)	0.5808 (3)	0.0241 (8)
C2	0.3140 (5)	0.2765 (2)	0.3371 (4)	0.0139 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Re1	0.01130 (11)	0.00960 (12)	0.01101 (12)	−0.00026 (6)	−0.00005 (7)	−0.00013 (6)
Cl1	0.0170 (5)	0.0123 (5)	0.0169 (5)	−0.0006 (4)	−0.0002 (4)	0.0005 (4)
C5	0.013 (2)	0.010 (2)	0.012 (2)	0.0021 (16)	−0.0005 (16)	0.0015 (16)
O5	0.0130 (16)	0.0202 (19)	0.0227 (17)	−0.0029 (13)	−0.0034 (13)	−0.0071 (14)
N3	0.0113 (17)	0.0110 (18)	0.0110 (17)	−0.0010 (14)	0.0013 (13)	0.0012 (14)
O4	0.0127 (15)	0.0161 (17)	0.0141 (15)	−0.0004 (12)	−0.0006 (12)	−0.0029 (13)
N2	0.017 (2)	0.026 (2)	0.0168 (19)	0.0039 (17)	0.0031 (16)	0.0009 (17)
N1	0.0121 (17)	0.0103 (19)	0.0172 (19)	−0.0001 (14)	0.0000 (14)	0.0036 (15)
C14	0.015 (2)	0.013 (2)	0.015 (2)	0.0012 (17)	0.0014 (17)	0.0052 (17)
C4	0.011 (2)	0.013 (2)	0.015 (2)	0.0013 (16)	0.0001 (16)	0.0019 (17)
C10	0.014 (2)	0.017 (2)	0.019 (2)	0.0022 (18)	0.0026 (18)	−0.0043 (19)
C15	0.015 (2)	0.024 (3)	0.016 (2)	0.0029 (19)	−0.0025 (17)	0.0024 (19)
C12	0.010 (2)	0.017 (2)	0.018 (2)	0.0019 (17)	0.0027 (16)	−0.0006 (18)
C17	0.023 (3)	0.020 (3)	0.022 (3)	0.000 (2)	0.002 (2)	−0.005 (2)
C1	0.023 (2)	0.009 (2)	0.016 (2)	0.0009 (18)	0.0019 (18)	−0.0015 (18)
C7	0.010 (2)	0.026 (3)	0.021 (2)	0.0035 (18)	0.0040 (17)	0.006 (2)
C16	0.014 (2)	0.010 (2)	0.017 (2)	−0.0034 (17)	0.0005 (17)	0.0017 (18)
C13	0.012 (2)	0.022 (3)	0.034 (3)	−0.0006 (19)	0.000 (2)	0.004 (2)
C8	0.015 (2)	0.018 (2)	0.017 (2)	0.0012 (18)	−0.0034 (17)	0.0026 (18)
C6	0.015 (2)	0.019 (3)	0.017 (2)	−0.0002 (18)	−0.0019 (17)	0.0016 (18)
C11	0.024 (3)	0.029 (3)	0.015 (2)	0.002 (2)	−0.0004 (19)	−0.005 (2)
C3	0.018 (2)	0.012 (2)	0.015 (2)	−0.0024 (17)	−0.0025 (18)	0.0039 (18)
O2	0.0225 (18)	0.0123 (17)	0.0272 (19)	−0.0016 (14)	0.0033 (15)	0.0027 (15)
O3	0.0279 (18)	0.0198 (19)	0.0170 (17)	0.0012 (15)	0.0096 (14)	−0.0011 (14)
O1	0.0222 (18)	0.021 (2)	0.0284 (19)	0.0010 (15)	−0.0097 (15)	−0.0060 (16)
C2	0.012 (2)	0.018 (2)	0.012 (2)	0.0026 (17)	0.0006 (16)	−0.0006 (18)

Geometric parameters (Å, º) top

Re1—C1	1.902 (5)	C15—H15C	0.96
Re1—C2	1.908 (5)	C15—H15A	0.96
Re1—C3	1.930 (5)	C12—C13	1.514 (6)
Re1—O4	2.149 (3)	C12—H12B	0.97
Re1—N1	2.172 (4)	C12—H12A	0.97
Re1—Cl1	2.4822 (12)	C17—C16	1.513 (6)
C5—N1	1.353 (6)	C17—H17B	0.96
C5—C6	1.379 (6)	C17—H17A	0.96
C5—C4	1.508 (6)	C17—H17C	0.96
O5—C4	1.231 (5)	C1—O1	1.156 (5)
N3—C14	1.514 (5)	C7—C8	1.383 (7)
N3—C12	1.517 (5)	C7—H7	0.93
N3—C16	1.518 (5)	C16—H16A	0.97
N3—C10	1.521 (5)	C16—H16B	0.97
O4—C4	1.282 (5)	C13—H13C	0.96
N2—C7	1.342 (6)	C13—H13B	0.96
N2—C6	1.344 (6)	C13—H13A	0.96
N1—C8	1.347 (6)	C8—H8	0.93
C14—C15	1.510 (6)	C6—H6	0.93
C14—H14B	0.97	C11—H11B	0.96
C14—H14A	0.97	C11—H11A	0.96
C10—C11	1.510 (6)	C11—H11C	0.96
C10—H10A	0.97	C3—O3	1.145 (5)
C10—H10B	0.97	O2—C2	1.156 (6)
C15—H15B	0.96

C1—Re1—C2	88.49 (19)	H15B—C15—H15C	109.5
C1—Re1—C3	89.99 (19)	C14—C15—H15A	109.5
C2—Re1—C3	87.95 (19)	H15B—C15—H15A	109.5
C1—Re1—O4	172.22 (16)	H15C—C15—H15A	109.5
C2—Re1—O4	96.95 (16)	C13—C12—N3	115.6 (4)
C3—Re1—O4	95.74 (16)	C13—C12—H12B	108.4
C1—Re1—N1	98.34 (17)	N3—C12—H12B	108.4
C2—Re1—N1	92.94 (16)	C13—C12—H12A	108.4
C3—Re1—N1	171.64 (16)	N3—C12—H12A	108.4
O4—Re1—N1	75.91 (13)	H12B—C12—H12A	107.4
C1—Re1—Cl1	91.55 (14)	C16—C17—H17B	109.5
C2—Re1—Cl1	178.07 (14)	C16—C17—H17A	109.5
C3—Re1—Cl1	93.98 (13)	H17B—C17—H17A	109.5
O4—Re1—Cl1	82.82 (9)	C16—C17—H17C	109.5
N1—Re1—Cl1	85.15 (10)	H17B—C17—H17C	109.5
N1—C5—C6	120.4 (4)	H17A—C17—H17C	109.5
N1—C5—C4	116.3 (4)	O1—C1—Re1	177.5 (4)
C6—C5—C4	123.3 (4)	N2—C7—C8	122.4 (4)
C14—N3—C12	109.0 (3)	N2—C7—H7	118.8
C14—N3—C16	111.4 (3)	C8—C7—H7	118.8
C12—N3—C16	108.3 (3)	C17—C16—N3	115.4 (4)
C14—N3—C10	108.7 (3)	C17—C16—H16A	108.4
C12—N3—C10	111.5 (3)	N3—C16—H16A	108.4
C16—N3—C10	108.0 (3)	C17—C16—H16B	108.4
C4—O4—Re1	118.2 (3)	N3—C16—H16B	108.4
C7—N2—C6	115.8 (4)	H16A—C16—H16B	107.5
C8—N1—C5	117.2 (4)	C12—C13—H13C	109.5
C8—N1—Re1	128.6 (3)	C12—C13—H13B	109.5
C5—N1—Re1	114.1 (3)	H13C—C13—H13B	109.5
C15—C14—N3	115.6 (4)	C12—C13—H13A	109.5
C15—C14—H14B	108.4	H13C—C13—H13A	109.5
N3—C14—H14B	108.4	H13B—C13—H13A	109.5
C15—C14—H14A	108.4	N1—C8—C7	121.1 (4)
N3—C14—H14A	108.4	N1—C8—H8	119.4
H14B—C14—H14A	107.4	C7—C8—H8	119.4
O5—C4—O4	126.7 (4)	N2—C6—C5	123.1 (4)
O5—C4—C5	118.0 (4)	N2—C6—H6	118.5
O4—C4—C5	115.3 (4)	C5—C6—H6	118.5
C11—C10—N3	115.3 (4)	C10—C11—H11B	109.5
C11—C10—H10A	108.4	C10—C11—H11A	109.5
N3—C10—H10A	108.4	H11B—C11—H11A	109.5
C11—C10—H10B	108.4	C10—C11—H11C	109.5
N3—C10—H10B	108.4	H11B—C11—H11C	109.5
H10A—C10—H10B	107.5	H11A—C11—H11C	109.5
C14—C15—H15B	109.5	O3—C3—Re1	177.0 (4)
C14—C15—H15C	109.5	O2—C2—Re1	177.3 (4)

Experimental details

Crystal data
Chemical formula	(C₈H₂₀N)[Re(C₅H₃N₂O₂)Cl(CO)₃]
M_r	559.02
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.927 (5), 22.278 (5), 10.903 (5)
β (°)	90.506 (5)
V (Å³)	1925.4 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.48
Crystal size (mm)	0.27 × 0.20 × 0.11

Data collection
Diffractometer	Bruker X8 APEXII 4K Kappa CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.273, 0.539
No. of measured, independent and observed [I > 2σ(I)] reflections	32482, 4781, 4121
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.098, 1.18
No. of reflections	4781
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.05, −1.38

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Acknowledgements

The authors thank Necsa and the UFS for funding and permission to publish this work.

References

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