Dichlorido{2-morpholino-N-[1-(2-pyrid­yl)ethyl­idene]ethanamine-κ3N,N′,N′′}manganese(II)

Ikmal Hisham, N.A.; Suleiman Gwaram, N.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536810050221

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page m41

https://doi.org/10.1107/S1600536810050221

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Dichlorido{2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³N,N′,N′′}manganese(II)

Nurul Azimah Ikmal Hisham,^a Nura Suleiman Gwaram,^a Hamid Khaledi ^a ^* and Hapipah Mohd Ali ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 29 November 2010; accepted 1 December 2010; online 4 December 2010)

In the title compound, [MnCl₂(C₁₃H₁₉N₃O)], the Mn^II ion is pentacoordinated in a distorted square-pyramidal geometry. The coordination environment is defined by the N,N′,N′′-tridentate Schiff base ligand and one Cl atom in the basal positions and one Cl atom in the apical position. In the crystal, intermolecular C—H⋯Cl hydrogen bonds link the molecules into a three-dimensional network. An intramolecular C—H⋯Cl hydrogen bond is also observed.

Related literature

For the crystal structure of the analogous Cd^II complex, see: Ikmal Hisham et al. (2010 ). For the crystal structure of [MnCl₂(C₂₄H₂₅N₃)], a structurally similar Mn^II complex, see: Schmiege et al. (2007 ).

Experimental

Crystal data

[MnCl₂(C₁₃H₁₉N₃O)]
M_r = 359.15
Monoclinic, P 2₁ /n
a = 9.6117 (6) Å
b = 13.8507 (8) Å
c = 12.1330 (7) Å
β = 106.738 (1)°
V = 1546.82 (16) Å³
Z = 4
Mo Kα radiation
μ = 1.20 mm⁻¹
T = 100 K
0.40 × 0.35 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.646, T_max = 0.754
15613 measured reflections
3543 independent reflections
3370 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.053
S = 1.11
3543 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cl1ⁱ	0.95	2.71	3.6257 (13)	163
C7—H7C⋯Cl2ⁱⁱ	0.98	2.75	3.6202 (13)	149
C8—H8A⋯Cl2ⁱⁱⁱ	0.99	2.83	3.7207 (14)	151
C12—H12B⋯Cl1	0.99	2.77	3.5904 (14)	141
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y, -z+1; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810050221/is2637sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050221/is2637Isup2.hkl

checkCIF report

Comment top

The title compound is isostructure to the recently reported Cd^II complex (Ikmal Hisham et al., 2010). The Mn^IIion is five-coordinated by the Schiff base 2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine and two Cl atoms in a distorted square-pyramidal environment (τ = 0.22). The Mn—Cl and Mn—N bond lengths in the present structure is similar to those in [MnCl₂(C₂₄H₂₅N₃)], the structurally closest Mn^II complex (Schmiege et al., 2007). In the crystal structure, intermolecular C—H···Cl hydrogen bonds link the adjacent molecules into a three-dimensional network. An intramolecular C—H···Cl hydrogen bonding has also been observed.

Related literature top

For the crystal structure of the analogous Cd^II complex, see: Ikmal Hisham et al. (2010). For the crystal structure of [MnCl₂(C₂₄H₂₅N₃)], a structurally similar Mn^II complex, see: Schmiege et al. (2007).

Experimental top

A mixture of 2-acetylpyridine (0.2 g, 1.65 mmol) and 4-(2-aminoethyl)morpholine (0.21 g, 1.65 mmol in ethanol (20 ml) was refluxed for 2 hr followed by addition of a solution of manganese(II) chloride (0.206 g, 1.65 mmol) in a minimum amount of water. The resulting solution was refluxed for 30 min, then set aside at room temperature. The crystals of the manganese(II) complex were obtained after a few days.

Structure description top

For the crystal structure of the analogous Cd^II complex, see: Ikmal Hisham et al. (2010). For the crystal structure of [MnCl₂(C₂₄H₂₅N₃)], a structurally similar Mn^II complex, see: Schmiege et al. (2007).

Computing details top

Data collection: APEX2 (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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot of the title compound at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii.

Dichlorido{2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³N,N',N''}manganese(II) top

Crystal data top

[MnCl₂(C₁₃H₁₉N₃O)]	F(000) = 740
M_r = 359.15	D_x = 1.542 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9925 reflections
a = 9.6117 (6) Å	θ = 2.2–31.4°
b = 13.8507 (8) Å	µ = 1.20 mm⁻¹
c = 12.1330 (7) Å	T = 100 K
β = 106.738 (1)°	Block, orange
V = 1546.82 (16) Å³	0.40 × 0.35 × 0.25 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3543 independent reflections
Radiation source: fine-focus sealed tube	3370 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
φ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.646, T_max = 0.754	k = −16→17
15613 measured reflections	l = −15→15

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.053	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0202P)² + 0.8164P] where P = (F_o² + 2F_c²)/3
3543 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

[MnCl₂(C₁₃H₁₉N₃O)]	V = 1546.82 (16) Å³
M_r = 359.15	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6117 (6) Å	µ = 1.20 mm⁻¹
b = 13.8507 (8) Å	T = 100 K
c = 12.1330 (7) Å	0.40 × 0.35 × 0.25 mm
β = 106.738 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3543 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3370 reflections with I > 2σ(I)
T_min = 0.646, T_max = 0.754	R_int = 0.019
15613 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	0 restraints
wR(F²) = 0.053	H-atom parameters constrained
S = 1.11	Δρ_max = 0.33 e Å⁻³
3543 reflections	Δρ_min = −0.23 e Å⁻³
182 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
Mn1	0.227997 (19)	0.094201 (13)	0.662679 (15)	0.01293 (6)
Cl1	0.46326 (3)	0.14018 (2)	0.77456 (2)	0.01695 (7)
Cl2	0.04111 (3)	0.21023 (2)	0.63296 (3)	0.01823 (7)
O1	0.18363 (10)	0.06033 (8)	1.01401 (8)	0.0220 (2)
N1	0.26463 (11)	0.11770 (8)	0.48657 (9)	0.0147 (2)
N2	0.24422 (11)	−0.04625 (8)	0.58539 (9)	0.0152 (2)
N3	0.15480 (11)	−0.01520 (8)	0.78545 (8)	0.0144 (2)
C1	0.25654 (14)	0.20208 (9)	0.43212 (11)	0.0176 (2)
H1	0.2251	0.2573	0.4647	0.021*
C2	0.29241 (14)	0.21242 (10)	0.32937 (11)	0.0195 (3)
H2	0.2854	0.2735	0.2926	0.023*
C3	0.33834 (14)	0.13223 (10)	0.28210 (11)	0.0198 (3)
H3	0.3649	0.1375	0.2127	0.024*
C4	0.34524 (13)	0.04350 (10)	0.33739 (11)	0.0172 (2)
H4	0.3760	−0.0127	0.3061	0.021*
C5	0.30645 (12)	0.03845 (9)	0.43907 (10)	0.0141 (2)
C6	0.29694 (13)	−0.05409 (9)	0.50011 (10)	0.0143 (2)
C7	0.34077 (14)	−0.14781 (9)	0.45884 (11)	0.0178 (2)
H7A	0.3963	−0.1860	0.5249	0.027*
H7B	0.4010	−0.1352	0.4076	0.027*
H7C	0.2537	−0.1837	0.4169	0.027*
C8	0.21498 (15)	−0.13062 (9)	0.64771 (11)	0.0184 (3)
H8A	0.3055	−0.1530	0.7043	0.022*
H8B	0.1756	−0.1841	0.5935	0.022*
C9	0.10472 (15)	−0.09964 (9)	0.70858 (11)	0.0187 (3)
H9A	0.0123	−0.0831	0.6503	0.022*
H9B	0.0856	−0.1544	0.7547	0.022*
C10	0.02951 (13)	0.01896 (10)	0.82360 (11)	0.0182 (3)
H10A	−0.0132	−0.0362	0.8544	0.022*
H10B	−0.0461	0.0455	0.7568	0.022*
C11	0.07601 (15)	0.09582 (10)	0.91531 (11)	0.0209 (3)
H11A	0.1154	0.1519	0.8835	0.025*
H11B	−0.0096	0.1179	0.9382	0.025*
C12	0.30849 (14)	0.03123 (10)	0.98074 (11)	0.0201 (3)
H12A	0.3838	0.0067	1.0490	0.024*
H12B	0.3490	0.0878	0.9507	0.024*
C13	0.27076 (14)	−0.04662 (10)	0.88940 (11)	0.0182 (2)
H13A	0.3589	−0.0638	0.8670	0.022*
H13B	0.2380	−0.1051	0.9217	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.01418 (10)	0.01214 (10)	0.01314 (9)	−0.00041 (7)	0.00499 (7)	−0.00097 (6)
Cl1	0.01485 (13)	0.01773 (15)	0.01853 (14)	−0.00194 (11)	0.00523 (11)	−0.00213 (11)
Cl2	0.01707 (14)	0.01822 (15)	0.01954 (14)	0.00326 (11)	0.00548 (11)	−0.00012 (11)
O1	0.0215 (5)	0.0319 (5)	0.0142 (4)	0.0012 (4)	0.0078 (4)	−0.0010 (4)
N1	0.0148 (5)	0.0144 (5)	0.0146 (5)	−0.0003 (4)	0.0039 (4)	−0.0008 (4)
N2	0.0172 (5)	0.0137 (5)	0.0144 (5)	−0.0015 (4)	0.0042 (4)	−0.0005 (4)
N3	0.0146 (5)	0.0154 (5)	0.0136 (5)	−0.0011 (4)	0.0045 (4)	−0.0010 (4)
C1	0.0190 (6)	0.0155 (6)	0.0177 (6)	0.0002 (5)	0.0043 (5)	−0.0003 (5)
C2	0.0216 (6)	0.0184 (6)	0.0172 (6)	−0.0021 (5)	0.0035 (5)	0.0030 (5)
C3	0.0205 (6)	0.0252 (7)	0.0139 (5)	−0.0032 (5)	0.0055 (5)	−0.0001 (5)
C4	0.0160 (6)	0.0193 (6)	0.0165 (6)	−0.0009 (5)	0.0049 (5)	−0.0031 (5)
C5	0.0116 (5)	0.0152 (6)	0.0141 (5)	−0.0004 (4)	0.0016 (4)	−0.0016 (4)
C6	0.0117 (5)	0.0148 (6)	0.0147 (5)	−0.0009 (4)	0.0011 (4)	−0.0023 (4)
C7	0.0185 (6)	0.0150 (6)	0.0206 (6)	0.0007 (5)	0.0067 (5)	−0.0030 (5)
C8	0.0265 (6)	0.0123 (6)	0.0172 (6)	−0.0025 (5)	0.0078 (5)	−0.0002 (5)
C9	0.0222 (6)	0.0161 (6)	0.0184 (6)	−0.0064 (5)	0.0068 (5)	−0.0016 (5)
C10	0.0143 (6)	0.0237 (7)	0.0179 (6)	−0.0007 (5)	0.0067 (5)	0.0016 (5)
C11	0.0215 (6)	0.0248 (7)	0.0185 (6)	0.0045 (5)	0.0090 (5)	0.0002 (5)
C12	0.0177 (6)	0.0277 (7)	0.0151 (6)	−0.0004 (5)	0.0050 (5)	−0.0006 (5)
C13	0.0185 (6)	0.0195 (6)	0.0159 (6)	0.0022 (5)	0.0039 (5)	0.0030 (5)

Geometric parameters (Å, º) top

Mn1—N2	2.1845 (11)	C4—H4	0.9500
Mn1—N1	2.2867 (10)	C5—C6	1.4963 (17)
Mn1—Cl2	2.3593 (4)	C6—C7	1.4949 (17)
Mn1—Cl1	2.3651 (4)	C7—H7A	0.9800
Mn1—N3	2.3694 (10)	C7—H7B	0.9800
O1—C11	1.4255 (16)	C7—H7C	0.9800
O1—C12	1.4300 (15)	C8—C9	1.5178 (18)
N1—C1	1.3337 (17)	C8—H8A	0.9900
N1—C5	1.3535 (16)	C8—H8B	0.9900
N2—C6	1.2811 (16)	C9—H9A	0.9900
N2—C8	1.4624 (16)	C9—H9B	0.9900
N3—C10	1.4864 (15)	C10—C11	1.5116 (18)
N3—C9	1.4869 (16)	C10—H10A	0.9900
N3—C13	1.4875 (16)	C10—H10B	0.9900
C1—C2	1.3932 (17)	C11—H11A	0.9900
C1—H1	0.9500	C11—H11B	0.9900
C2—C3	1.3796 (19)	C12—C13	1.5135 (18)
C2—H2	0.9500	C12—H12A	0.9900
C3—C4	1.3925 (19)	C12—H12B	0.9900
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.3896 (17)	C13—H13B	0.9900

N2—Mn1—N1	71.12 (4)	C6—C7—H7B	109.5
N2—Mn1—Cl2	133.34 (3)	H7A—C7—H7B	109.5
N1—Mn1—Cl2	94.33 (3)	C6—C7—H7C	109.5
N2—Mn1—Cl1	108.15 (3)	H7A—C7—H7C	109.5
N1—Mn1—Cl1	96.83 (3)	H7B—C7—H7C	109.5
Cl2—Mn1—Cl1	117.667 (13)	N2—C8—C9	106.90 (10)
N2—Mn1—N3	76.77 (4)	N2—C8—H8A	110.3
N1—Mn1—N3	146.31 (4)	C9—C8—H8A	110.3
Cl2—Mn1—N3	100.42 (3)	N2—C8—H8B	110.3
Cl1—Mn1—N3	102.67 (3)	C9—C8—H8B	110.3
C11—O1—C12	108.96 (9)	H8A—C8—H8B	108.6
C1—N1—C5	118.81 (11)	N3—C9—C8	112.48 (10)
C1—N1—Mn1	125.80 (8)	N3—C9—H9A	109.1
C5—N1—Mn1	115.27 (8)	C8—C9—H9A	109.1
C6—N2—C8	121.97 (11)	N3—C9—H9B	109.1
C6—N2—Mn1	121.06 (9)	C8—C9—H9B	109.1
C8—N2—Mn1	116.20 (8)	H9A—C9—H9B	107.8
C10—N3—C9	107.50 (10)	N3—C10—C11	111.04 (10)
C10—N3—C13	107.79 (9)	N3—C10—H10A	109.4
C9—N3—C13	109.27 (10)	C11—C10—H10A	109.4
C10—N3—Mn1	113.96 (8)	N3—C10—H10B	109.4
C9—N3—Mn1	102.11 (7)	C11—C10—H10B	109.4
C13—N3—Mn1	115.75 (7)	H10A—C10—H10B	108.0
N1—C1—C2	122.63 (12)	O1—C11—C10	111.39 (11)
N1—C1—H1	118.7	O1—C11—H11A	109.3
C2—C1—H1	118.7	C10—C11—H11A	109.3
C3—C2—C1	118.72 (12)	O1—C11—H11B	109.3
C3—C2—H2	120.6	C10—C11—H11B	109.3
C1—C2—H2	120.6	H11A—C11—H11B	108.0
C2—C3—C4	119.13 (12)	O1—C12—C13	111.34 (11)
C2—C3—H3	120.4	O1—C12—H12A	109.4
C4—C3—H3	120.4	C13—C12—H12A	109.4
C5—C4—C3	118.98 (12)	O1—C12—H12B	109.4
C5—C4—H4	120.5	C13—C12—H12B	109.4
C3—C4—H4	120.5	H12A—C12—H12B	108.0
N1—C5—C4	121.71 (11)	N3—C13—C12	112.05 (11)
N1—C5—C6	114.59 (10)	N3—C13—H13A	109.2
C4—C5—C6	123.57 (11)	C12—C13—H13A	109.2
N2—C6—C7	124.01 (12)	N3—C13—H13B	109.2
N2—C6—C5	114.95 (11)	C12—C13—H13B	109.2
C7—C6—C5	120.98 (11)	H13A—C13—H13B	107.9
C6—C7—H7A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cl1ⁱ	0.95	2.71	3.6257 (13)	163
C7—H7C···Cl2ⁱⁱ	0.98	2.75	3.6202 (13)	149
C8—H8A···Cl2ⁱⁱⁱ	0.99	2.83	3.7207 (14)	151
C12—H12B···Cl1	0.99	2.77	3.5904 (14)	141

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y, −z+1; (iii) −x+1/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[MnCl₂(C₁₃H₁₉N₃O)]
M_r	359.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.6117 (6), 13.8507 (8), 12.1330 (7)
β (°)	106.738 (1)
V (Å³)	1546.82 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.20
Crystal size (mm)	0.40 × 0.35 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.646, 0.754
No. of measured, independent and observed [I > 2σ(I)] reflections	15613, 3543, 3370
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.053, 1.11
No. of reflections	3543
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cl1ⁱ	0.95	2.71	3.6257 (13)	162.6
C7—H7C···Cl2ⁱⁱ	0.98	2.75	3.6202 (13)	148.7
C8—H8A···Cl2ⁱⁱⁱ	0.99	2.83	3.7207 (14)	150.7
C12—H12B···Cl1	0.99	2.77	3.5904 (14)	141.0

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y, −z+1; (iii) −x+1/2, y−1/2, −z+3/2.

Acknowledgements

The authors thank University of Malaya for funding this study (UMRG grant RG024/09BIO).

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