fac-Tricarbon­yl(pyridine-κN)(1,1,1-trifluoro­acetyl­acetonato-κ2O,O′)rhenium(I)

Visser, H.G.; Roodt, A.; Volmink, A.; Kemp, G.

doi:10.1107/S160053681104476X

metal-organic compounds

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Volume 67| Part 11| November 2011| Page m1631

doi:10.1107/S160053681104476X

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fac-Tricarbonyl(pyridine-κN)(1,1,1-trifluoroacetylacetonato-κ²O,O′)rhenium(I)

Hendrik G. Visser,^a ^* Andreas Roodt,^a Amanda-lee Volmink ^a and Gerdus Kemp ^b

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa, and ^bPetlabs, Little Company of Mary Hospital, Pretoria 0001 9300, South Africa
^*Correspondence e-mail: visserhg@ufs.ac.za

(Received 24 October 2011; accepted 26 October 2011; online 29 October 2011)

In the title compound, [Re(C₅H₄F₃O₂)(C₅H₅N)(CO)₃], the Re^I atom is six-coordinated owing to bonding by three carbonyl ligands arranged in a fac configuration, two O atoms from the bidentate 1,1,1-trifluoroacetylacetonate ligand and an N atom from a pyridine ligand. In the crystal, the molecules pack in layers, diagonally, in a head-to-tail fashion across the ab plane. These layers are stabilsed by intermolecular C—H⋯O and C—H⋯F hydrogen bonds.

Related literature

For the synthesis of the Re(I)-tricarbonyl synthon, see: Alberto et al. (1996 ). For related rhenium–tricarbonyl complexes, see: Brink et al. (2009 , 2011 ); Mundwiler et al. (2004 ); Schutte et al. (2010 ). For a review on structure–reactivity relationships, see: Roodt et al. (2011 ).

Experimental

Crystal data

[Re(C₅H₄F₃O₂)(C₅H₅N)(CO)₃]
M_r = 502.41
Monoclinic, P 2₁ /c
a = 15.561 (2) Å
b = 6.982 (3) Å
c = 14.082 (5) Å
β = 103.271 (5)°
V = 1489.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 8.22 mm⁻¹
T = 100 K
0.15 × 0.10 × 0.03 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.328, T_max = 0.778
17351 measured reflections
3603 independent reflections
3104 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.059
S = 1.06
3603 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 1.43 e Å⁻³
Δρ_min = −1.09 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯F3ⁱ	0.93	2.55	3.407 (6)	153
C22—H22⋯O1ⁱⁱ	0.93	2.58	3.360 (5)	142
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; 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: 10.1107/S160053681104476X/ng5257sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681104476X/ng5257Isup2.hkl

checkCIF report

Comment top

This work forms part of our ongoing research in structure/reactivity relationships (Roodt et al., 2011) and the applications of rhenium- tricarbonyl complexes in the radiopharmaceutical industry (Brink et al., 2009, 2011; Schutte et al., 2010).

In the title Rhenium(I) compound, [Re(C₅F₃H₄O₂)(CO)₃(py)], each rhenium atom is six-coordinated to three carbonyl ligands, two oxygen atoms from the bidentate 1,1,1-trifluoroacetylacetonato ligand and a nitrogen atom from a pyridine ligand to form a slightly distorted octahedron (see Figure 1). This is illustrated by the small deviations from 90 °, with the O1—Re1—N1 being the furthest outlier (82.72 (11) Å. All the bonding distances and angles are considered normal (Mundwiler et al. 2004); Brink et al. 2009, 2011). The three carbonyl ligands are arranged in a facial configuration around the Re atom.

Interestingly, it does not seem as if the electronwithdrawing properties of the fluorine molecules on the bidentate ligand backbone have any effect on bonding distances in the molecule (as opposed to the methyl group). The trans Re—C bonding distances are exactly the same (Re1—C12; Re1—C13; 1.906 (4) Å) while the Re1—O2 distance of 2.117 (3) Å is similar to Re1—O1 within experimental error (2.135 (3) Å).

The molecules pack in layers, diagonally, in a head-to-tail fashion across the ab plane. These layers are stabilsed by intermolecular CH–O and CH–F hydrogen bonds (see Figure 2).

Related literature top

For the synthesis of the Re(I)-tricarbonyl synthon, see: Alberto et al. (1996). For related rhenium–tricarbonyl complexes, see: Brink et al. (2009, 2011); Mundwiler et al. (2004); Schutte et al. (2010). For a review on structure–reactivity relationships, see: Roodt et al. (2011).

Experimental top

[Re(CO)₃(Br)₃] (500 mg; 0.648 mmol) was prepared according to the method of Alberto (Alberto et al., 1996) and was dissolved in 10 ml water (pH 2.2) while stirring for 30 min. To this solution, AgNO₃ (330 mg; 1.945 mmol) was added and stirred for 24 h at room temperature. The precipitate, AgBr, was filtered off after which trifluoroacetylacetone (0.1 g; 0.649 mmol) was added to the filtrate and stirred for another 48 hrs. To the yellow solution, pyridine (0.0512 g; 0.648 mmol) was added and stirred for 10 min. at room temperature. A bright yellow precipitate formed which was filtered off and recrystallized from acetone (3 ml). Yellow needles were obtained (yield = 0.292 g; 89%)

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (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. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing and hydrogen bonding as observed across the ab plane. Symmetry codes: (i) 1 - x, 1 - y, -z, (ii) x, y + 1, z.

fac-Tricarbonyl(pyridine-κN)(1,1,1-trifluoroacetylacetonato- κ²O,O')rhenium(I) top

Crystal data top

[Re(C₅H₄F₃O₂)(C₅H₅N)(CO)₃]	F(000) = 944
M_r = 502.41	D_x = 2.241 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7262 reflections
a = 15.561 (2) Å	θ = 2.7–28.2°
b = 6.982 (3) Å	µ = 8.22 mm⁻¹
c = 14.082 (5) Å	T = 100 K
β = 103.271 (5)°	Needle, yellow
V = 1489.1 (9) Å³	0.15 × 0.1 × 0.03 mm
Z = 4

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	3603 independent reflections
Radiation source: fine-focus sealed tube	3104 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 28°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −20→20
T_min = 0.328, T_max = 0.778	k = −9→9
17351 measured reflections	l = −18→16

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0265P)² + 2.5868P] where P = (F_o² + 2F_c²)/3
3603 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 1.43 e Å⁻³
0 restraints	Δρ_min = −1.09 e Å⁻³

Crystal data top

[Re(C₅H₄F₃O₂)(C₅H₅N)(CO)₃]	V = 1489.1 (9) Å³
M_r = 502.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.561 (2) Å	µ = 8.22 mm⁻¹
b = 6.982 (3) Å	T = 100 K
c = 14.082 (5) Å	0.15 × 0.1 × 0.03 mm
β = 103.271 (5)°

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	3603 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3104 reflections with I > 2σ(I)
T_min = 0.328, T_max = 0.778	R_int = 0.040
17351 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 1.06	Δρ_max = 1.43 e Å⁻³
3603 reflections	Δρ_min = −1.09 e Å⁻³
209 parameters

Special details top

Experimental. The intensity data were collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 40 s/frame. A total of 1709 frames were collected with a frame width of 0.5° covering up to θ = 28.39° with 99.9% completeness accomplished.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.3352 (3)	0.1319 (6)	0.0313 (3)	0.0209 (9)
C2	0.3897 (3)	0.2909 (6)	0.0641 (3)	0.0233 (9)
H2	0.436	0.3153	0.0341	0.028*
C3	0.3793 (3)	0.4120 (6)	0.1371 (3)	0.0211 (9)
C4	0.3568 (3)	0.0060 (7)	−0.0476 (3)	0.0289 (10)
H4A	0.3044	−0.0147	−0.0978	0.043*
H4B	0.3791	−0.1148	−0.0199	0.043*
H4C	0.4006	0.0677	−0.0751	0.043*
C5	0.4426 (3)	0.5780 (7)	0.1659 (4)	0.0292 (10)
C11	0.2715 (3)	0.0553 (6)	0.2774 (3)	0.0224 (9)
C12	0.1608 (3)	0.3619 (6)	0.2583 (3)	0.0193 (8)
C13	0.1142 (3)	0.0508 (6)	0.1529 (3)	0.0178 (8)
C21	0.1734 (3)	0.5963 (6)	0.0479 (3)	0.0189 (8)
H21	0.2129	0.6478	0.1015	0.023*
C22	0.1372 (3)	0.7145 (5)	−0.0285 (3)	0.0205 (9)
H22	0.1524	0.8436	−0.0264	0.025*
C23	0.0777 (3)	0.6403 (6)	−0.1093 (3)	0.0205 (9)
H23	0.0527	0.718	−0.1621	0.025*
C24	0.0567 (3)	0.4488 (6)	−0.1089 (3)	0.0187 (8)
H24	0.0164	0.3954	−0.1613	0.022*
C25	0.0959 (3)	0.3368 (6)	−0.0305 (3)	0.0178 (8)
H25	0.0819	0.2072	−0.0318	0.021*
N1	0.1538 (2)	0.4066 (5)	0.0481 (2)	0.0149 (7)
O1	0.26931 (19)	0.0826 (4)	0.0638 (2)	0.0193 (6)
O2	0.32142 (19)	0.4095 (4)	0.1875 (2)	0.0192 (6)
O11	0.3032 (2)	−0.0437 (5)	0.3404 (2)	0.0356 (8)
O12	0.1301 (2)	0.4540 (4)	0.3090 (2)	0.0274 (7)
O13	0.0548 (2)	−0.0508 (4)	0.1444 (2)	0.0237 (7)
F1	0.4843 (2)	0.5667 (5)	0.2568 (2)	0.0587 (10)
F2	0.3971 (3)	0.7446 (4)	0.1556 (3)	0.0615 (11)
F3	0.5014 (2)	0.5958 (6)	0.1124 (3)	0.0682 (11)
Re1	0.213272 (11)	0.21860 (2)	0.171210 (11)	0.01468 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.023 (2)	0.020 (2)	0.019 (2)	0.0079 (17)	0.0038 (17)	0.0041 (17)
C2	0.017 (2)	0.031 (2)	0.024 (2)	−0.0022 (18)	0.0096 (19)	0.0017 (18)
C3	0.017 (2)	0.022 (2)	0.024 (2)	−0.0005 (17)	0.0029 (18)	0.0071 (17)
C4	0.032 (3)	0.029 (2)	0.029 (2)	0.005 (2)	0.015 (2)	−0.0023 (19)
C5	0.026 (3)	0.031 (2)	0.033 (3)	−0.010 (2)	0.011 (2)	−0.001 (2)
C11	0.022 (2)	0.020 (2)	0.025 (2)	−0.0016 (17)	0.0051 (19)	−0.0013 (17)
C12	0.022 (2)	0.0168 (19)	0.020 (2)	−0.0029 (16)	0.0072 (17)	0.0033 (16)
C13	0.024 (2)	0.0153 (19)	0.015 (2)	0.0023 (16)	0.0068 (17)	−0.0007 (15)
C21	0.021 (2)	0.0140 (18)	0.022 (2)	−0.0033 (16)	0.0064 (18)	−0.0050 (16)
C22	0.025 (2)	0.0113 (17)	0.027 (2)	−0.0011 (16)	0.0108 (19)	−0.0009 (16)
C23	0.026 (2)	0.0166 (19)	0.020 (2)	0.0018 (17)	0.0068 (18)	0.0042 (16)
C24	0.020 (2)	0.021 (2)	0.015 (2)	0.0006 (16)	0.0035 (17)	−0.0022 (15)
C25	0.022 (2)	0.0154 (17)	0.017 (2)	−0.0015 (16)	0.0072 (17)	−0.0024 (16)
N1	0.0179 (18)	0.0149 (15)	0.0124 (16)	−0.0004 (13)	0.0049 (14)	−0.0005 (12)
O1	0.0229 (16)	0.0155 (13)	0.0214 (15)	0.0009 (12)	0.0093 (13)	−0.0006 (11)
O2	0.0173 (15)	0.0203 (14)	0.0205 (15)	−0.0051 (11)	0.0056 (12)	−0.0016 (12)
O11	0.039 (2)	0.0347 (19)	0.0300 (19)	0.0023 (15)	0.0004 (16)	0.0119 (15)
O12	0.036 (2)	0.0215 (15)	0.0304 (18)	0.0001 (13)	0.0198 (15)	−0.0045 (13)
O13	0.0219 (17)	0.0196 (15)	0.0309 (17)	−0.0074 (13)	0.0089 (14)	−0.0033 (13)
F1	0.059 (2)	0.057 (2)	0.050 (2)	−0.0246 (18)	−0.0092 (18)	−0.0007 (17)
F2	0.050 (2)	0.0276 (16)	0.104 (3)	−0.0086 (15)	0.011 (2)	0.0036 (18)
F3	0.060 (2)	0.070 (2)	0.088 (3)	−0.034 (2)	0.045 (2)	−0.019 (2)
Re1	0.01714 (10)	0.01195 (8)	0.01581 (9)	−0.00153 (6)	0.00557 (6)	−0.00083 (6)

Geometric parameters (Å, º) top

C1—O1	1.263 (5)	C13—O13	1.150 (5)
C1—C2	1.409 (6)	C13—Re1	1.906 (4)
C1—C4	1.513 (6)	C21—N1	1.360 (5)
C2—C3	1.369 (6)	C21—C22	1.370 (6)
C2—H2	0.93	C21—H21	0.93
C3—O2	1.269 (5)	C22—C23	1.392 (6)
C3—C5	1.514 (6)	C22—H22	0.93
C4—H4A	0.96	C23—C24	1.377 (6)
C4—H4B	0.96	C23—H23	0.93
C4—H4C	0.96	C24—C25	1.376 (6)
C5—F1	1.298 (6)	C24—H24	0.93
C5—F3	1.317 (5)	C25—N1	1.347 (5)
C5—F2	1.353 (6)	C25—H25	0.93
C11—O11	1.144 (5)	N1—Re1	2.202 (3)
C11—Re1	1.932 (5)	O1—Re1	2.135 (3)
C12—O12	1.143 (5)	O2—Re1	2.117 (3)
C12—Re1	1.906 (4)

O1—C1—C2	125.0 (4)	C24—C23—C22	118.2 (4)
O1—C1—C4	116.3 (4)	C24—C23—H23	120.9
C2—C1—C4	118.7 (4)	C22—C23—H23	120.9
C3—C2—C1	124.6 (4)	C25—C24—C23	119.6 (4)
C3—C2—H2	117.7	C25—C24—H24	120.2
C1—C2—H2	117.7	C23—C24—H24	120.2
O2—C3—C2	129.2 (4)	N1—C25—C24	122.9 (4)
O2—C3—C5	111.3 (4)	N1—C25—H25	118.6
C2—C3—C5	119.5 (4)	C24—C25—H25	118.6
C1—C4—H4A	109.5	C25—N1—C21	117.3 (3)
C1—C4—H4B	109.5	C25—N1—Re1	120.8 (3)
H4A—C4—H4B	109.5	C21—N1—Re1	121.9 (3)
C1—C4—H4C	109.5	C1—O1—Re1	129.3 (3)
H4A—C4—H4C	109.5	C3—O2—Re1	126.7 (3)
H4B—C4—H4C	109.5	C12—Re1—C13	87.55 (17)
F1—C5—F3	108.3 (4)	C12—Re1—C11	90.32 (18)
F1—C5—F2	106.8 (4)	C13—Re1—C11	87.88 (18)
F3—C5—F2	105.9 (4)	C12—Re1—O2	92.70 (14)
F1—C5—C3	111.4 (4)	C13—Re1—O2	178.20 (14)
F3—C5—C3	114.4 (4)	C11—Re1—O2	93.89 (15)
F2—C5—C3	109.7 (4)	C12—Re1—O1	174.14 (14)
O11—C11—Re1	177.7 (4)	C13—Re1—O1	94.59 (14)
O12—C12—Re1	177.4 (3)	C11—Re1—O1	95.20 (15)
O13—C13—Re1	178.3 (4)	O2—Re1—O1	84.99 (11)
N1—C21—C22	122.5 (4)	C12—Re1—N1	91.68 (15)
N1—C21—H21	118.8	C13—Re1—N1	94.55 (15)
C22—C21—H21	118.8	C11—Re1—N1	176.91 (15)
C21—C22—C23	119.6 (4)	O2—Re1—N1	83.67 (12)
C21—C22—H22	120.2	O1—Re1—N1	82.72 (11)
C23—C22—H22	120.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F3ⁱ	0.93	2.55	3.407 (6)	153
C22—H22···O1ⁱⁱ	0.93	2.58	3.360 (5)	142

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

Experimental details

Crystal data
Chemical formula	[Re(C₅H₄F₃O₂)(C₅H₅N)(CO)₃]
M_r	502.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.561 (2), 6.982 (3), 14.082 (5)
β (°)	103.271 (5)
V (Å³)	1489.1 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.22
Crystal size (mm)	0.15 × 0.1 × 0.03

Data collection
Diffractometer	Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.328, 0.778
No. of measured, independent and observed [I > 2σ(I)] reflections	17351, 3603, 3104
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.059, 1.06
No. of reflections	3603
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.43, −1.09

Computer programs: APEX2 (Bruker, 2010), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F3ⁱ	0.93	2.55	3.407 (6)	152.9
C22—H22···O1ⁱⁱ	0.93	2.58	3.360 (5)	142

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

Acknowledgements

Financial assistance from the University of the Free State and Ntembi is gratefully acknowledged.

References

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