Dicarbonyl­dichlorido(N,N,N′,N′-tetra­methyl­ethylenediamine)­ruthenium(II)

Baghlaf, A.O.; Ishaq, M.; Al-Juaid, S.S.; Asiri, A.M.; Arshad, M.N.

doi:10.1107/S1600536811022227

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m925

doi:10.1107/S1600536811022227

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Dicarbonyldichlorido(N,N,N′,N′-tetramethylethylenediamine)ruthenium(II)

Ahmad O. Baghlaf,^a Muhammad Ishaq,^a Salih S. Al-Juaid,^a Abdullah M. Asiri ^b ‡ and Muhammad Nadeem Arshad ^c ^*

^aChemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, ^bThe Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah, PO Box 80203, Saudi Arabia, and ^cX-ray Diffraction and Crystallography Laboratory, Department of Physics, School of Physical Sciences, University of the Punjab, Quaid-e-Azam Campus, Lahore-54590, Pakistan
^*Correspondence e-mail: mnachemist@hotmail.com

(Received 31 May 2011; accepted 8 June 2011; online 18 June 2011)

In the title compound, [RuCl₂(C₆H₁₆N₂)(CO)₂], the geometry around the Ru^II atom is a distorted RuC₂N₂Cl₂ octahedron, with pairs of C and Cl atoms trans to each other and the N atoms of the bidentate ligand in a cis conformation. The five-membered chelate ring is puckered on the C—C bond.

Related literature

For background to ruthenium carbonyl derivatives, see: Manchot & Konig (1924 ); Stephenson & Wilkinson (1966 ); Kingston et al. (1967 ); Baghlaf et al. (2007 ); Campbell (1975 ); Padhey & Kaufman (1985 ). For a related structure, see: Bakar et al. (1993 ).

Experimental

Crystal data

[RuCl₂(C₆H₁₆N₂)(CO)₂]
M_r = 344.20
Monoclinic, P 2₁ /c
a = 7.463 (6) Å
b = 14.579 (6) Å
c = 12.718 (12) Å
β = 106.37 (8)°
V = 1327.7 (17) Å³
Z = 4
Mo Kα radiation
μ = 1.57 mm⁻¹
T = 160 K
0.38 × 0.38 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.591, T_max = 0.69
3153 measured reflections
2877 independent reflections
2644 reflections with I > 2σ(I)
R_int = 0.015
2 standard reflections every 100 reflections intensity decay: 5%

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.061
S = 1.07
2877 reflections
184 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.06 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ru1—C1	1.872 (3)
Ru1—C2	1.872 (2)
Ru1—N2	2.211 (2)
Ru1—N1	2.220 (2)
Ru1—Cl1	2.413 (2)
Ru1—Cl2	2.408 (2)

N2—Ru1—N1	82.75 (9)

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811022227/hb5901sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022227/hb5901Isup2.hkl

checkCIF report

Comment top

The salt [Ru(CO)2Cl2]n was first reported by (Manchot & Konig, 1924) but its importance and chemistry was shown in late 1960's by (Stephenson & Wilkinson, 1966), (Kingston et al., 1967) who have reported several compounds of the type [Ru(CO)2Cl2L2] where L=monodentate ligand. This was due to the fact that the salt [Ru(CO)2Cl2]n has proved a useful precursor for the synthesis of a variety of organometallic compounds. We have also reported from our laboratories compounds with ligands containing N, O and S atom as electron donor (e.g. Baghlaf et al., 2007). However (Campbell (1975) and Padhey & Kaufman (1985) have reported about remarkable biological activities of such compounds against microbes, viruses and tumours. This has been the main reason for our research activity in the field of bio-inorganic chemistry of transition metal complexes. The metal atom Ru in the salt [Ru(CO)2Cl2]n being electron deficient acts as electron acceptor. This enhances its ability to coordinate with electron donor ligand (TMEDA) to give a stable octahedral electron rich compound of low ionization energy [Ru(CO)2Cl2TMEDA]. The bidentate nature of the ligand (TMEDA) has also been reported in the X-ray structure of the complex [Mo(CO)₄TMEDA] by (Bakar et al., 1993).

In the crystal structure of title compound, ruthenium atom is almost octahedrally coordinated to the two nitrogen-donors atoms of tetramethyl ethylene-1,2-diamine (TMEDA), two chloro and two carbonyl groups. A five membered non-planer ring formed through Ru1/N1/C5/C6/N2 as both of the carbon atoms are sp³ hybridized. The root mean square deniavtion for the ring measure 0.2149Å with the maximum deviation from C5 and C6 measures -0.2999 (19) Å and 0.3144 (19)Å respectively.

Related literature top

For background to ruthenium carbonyl derivatives, see: Manchot & Konig (1924); Stephenson & Wilkinson (1966); Kingston et al. (1967); Baghlaf et al., (2007); Campbell (1975). Padhey & Kaufman (1985). For a related structure, see: Bakar et al. (1993).

Experimental top

In a 100-ml round bottom flask fitted with nitrogen gas inlet, water condenser and magnetic stirrer was added 0.2 g of [Ru(CO)₂ Cl₂]n and 0.5 ml of tetramethylethylene diamine (TMEDA) in 15 ml MeOH. The reaction mixture was heated at about 70 °C for 1 h. The yellow green solution was reduced in volume and passed through a small alumina column (15 g. Al₂O₃). The yellow band was eluted with MeOH. The solvent was reduced in volume and on cooling it gave yellow blocks of (I). Yield 70%.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); 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. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Unit cell packing for (I).

Dicarbonyldichlorido(N,N,N',N'- tetramethylethylenediamine)ruthenium(II) top

Crystal data top

[RuCl₂(C₆H₁₆N₂)(CO)₂]	F(000) = 688
M_r = 344.20	D_x = 1.722 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 493 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.463 (6) Å	Cell parameters from 25 reflections
b = 14.579 (6) Å	θ = 10.6–14.0°
c = 12.718 (12) Å	µ = 1.57 mm⁻¹
β = 106.37 (8)°	T = 160 K
V = 1327.7 (17) Å³	Block, yellow
Z = 4	0.38 × 0.38 × 0.25 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2644 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.015
Graphite monochromator	θ_max = 27.0°, θ_min = 2.2°
Nonprofiled ω/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→18
T_min = 0.591, T_max = 0.69	l = 0→16
3153 measured reflections	2 standard reflections every 100 reflections
2877 independent reflections	intensity decay: 5%

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0385P)² + 0.6002P] where P = (F_o² + 2F_c²)/3
2877 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 1.06 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[RuCl₂(C₆H₁₆N₂)(CO)₂]	V = 1327.7 (17) Å³
M_r = 344.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.463 (6) Å	µ = 1.57 mm⁻¹
b = 14.579 (6) Å	T = 160 K
c = 12.718 (12) Å	0.38 × 0.38 × 0.25 mm
β = 106.37 (8)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2644 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.015
T_min = 0.591, T_max = 0.69	2 standard reflections every 100 reflections
3153 measured reflections	intensity decay: 5%
2877 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 1.06 e Å⁻³
2877 reflections	Δρ_min = −0.48 e Å⁻³
184 parameters

Special details top

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 > 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	−0.0497 (3)	0.14822 (15)	0.31835 (17)	0.0244 (4)
C2	0.1219 (3)	−0.01145 (15)	0.39077 (17)	0.0237 (4)
C3	0.5479 (3)	0.00447 (17)	0.3248 (2)	0.0269 (4)
H3A	0.634 (4)	−0.025 (2)	0.292 (2)	0.032*
H3B	0.542 (4)	−0.025 (2)	0.386 (2)	0.032*
H3C	0.587 (4)	0.065 (2)	0.342 (2)	0.032*
C4	0.3204 (4)	−0.09661 (19)	0.2146 (3)	0.0397 (6)
H4A	0.197 (5)	−0.105 (2)	0.163 (3)	0.048*
H4B	0.331 (4)	−0.131 (2)	0.294 (3)	0.048*
H4C	0.417 (5)	−0.121 (2)	0.187 (3)	0.048*
C5	0.3756 (4)	0.0491 (2)	0.1397 (2)	0.0376 (6)
H5A	0.269 (5)	0.028 (2)	0.078 (3)	0.045*
H5B	0.496 (5)	0.032 (2)	0.127 (3)	0.045*
C6	0.3660 (4)	0.1513 (2)	0.1516 (2)	0.0362 (6)
H6A	0.459 (5)	0.170 (2)	0.218 (3)	0.043*
H6B	0.373 (4)	0.180 (2)	0.087 (3)	0.043*
C7	0.0379 (4)	0.17649 (19)	0.0602 (2)	0.0352 (5)
H7A	−0.077 (5)	0.197 (2)	0.078 (2)	0.042*
H7B	0.026 (4)	0.115 (2)	0.023 (3)	0.042*
H7C	0.077 (4)	0.219 (2)	0.010 (3)	0.042*
C8	0.1967 (4)	0.27503 (17)	0.2056 (2)	0.0385 (6)
H8A	0.229 (5)	0.311 (2)	0.152 (3)	0.046*
H8B	0.285 (5)	0.285 (2)	0.277 (3)	0.046*
H8C	0.075 (5)	0.294 (2)	0.214 (2)	0.046*
Cl1	0.36315 (7)	0.16019 (4)	0.43227 (4)	0.02799 (12)
Cl2	−0.09471 (7)	−0.00421 (4)	0.15266 (4)	0.02621 (12)
O1	−0.1658 (2)	0.19233 (12)	0.33235 (15)	0.0343 (4)
O2	0.1117 (3)	−0.06675 (12)	0.45157 (15)	0.0377 (4)
Ru1	0.14044 (2)	0.078019 (10)	0.288724 (12)	0.01683 (7)
N1	0.3635 (2)	0.00254 (13)	0.24068 (15)	0.0233 (4)
N2	0.1815 (3)	0.17845 (13)	0.16732 (15)	0.0246 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0238 (10)	0.0231 (10)	0.0239 (10)	−0.0067 (9)	0.0027 (8)	−0.0024 (8)
C2	0.0224 (10)	0.0243 (10)	0.0224 (9)	−0.0033 (8)	0.0034 (8)	−0.0050 (8)
C3	0.0185 (10)	0.0303 (12)	0.0289 (11)	0.0033 (9)	0.0018 (8)	0.0029 (9)
C4	0.0287 (12)	0.0310 (13)	0.0561 (18)	0.0060 (10)	0.0064 (12)	−0.0169 (12)
C5	0.0329 (13)	0.0558 (16)	0.0263 (12)	0.0170 (12)	0.0120 (10)	0.0091 (11)
C6	0.0270 (12)	0.0467 (15)	0.0368 (13)	0.0019 (11)	0.0119 (10)	0.0174 (12)
C7	0.0338 (13)	0.0380 (14)	0.0281 (12)	0.0010 (11)	−0.0007 (10)	0.0110 (10)
C8	0.0492 (16)	0.0200 (11)	0.0423 (14)	−0.0074 (11)	0.0065 (12)	0.0060 (10)
Cl1	0.0275 (3)	0.0288 (3)	0.0241 (2)	−0.0044 (2)	0.0016 (2)	−0.0063 (2)
Cl2	0.0198 (2)	0.0304 (3)	0.0266 (2)	−0.00546 (19)	0.00355 (19)	−0.0077 (2)
O1	0.0267 (8)	0.0290 (9)	0.0485 (10)	0.0042 (7)	0.0129 (7)	−0.0069 (7)
O2	0.0473 (11)	0.0342 (9)	0.0326 (9)	−0.0072 (8)	0.0129 (8)	0.0088 (8)
Ru1	0.01583 (10)	0.01612 (10)	0.01779 (10)	−0.00122 (5)	0.00351 (7)	−0.00079 (5)
N1	0.0207 (8)	0.0256 (9)	0.0229 (8)	0.0035 (7)	0.0049 (7)	−0.0021 (7)
N2	0.0242 (9)	0.0230 (9)	0.0244 (9)	−0.0019 (7)	0.0035 (7)	0.0046 (7)

Geometric parameters (Å, º) top

Ru1—C1	1.872 (3)	C5—N1	1.477 (3)
Ru1—C2	1.872 (2)	C5—C6	1.502 (4)
Ru1—N2	2.211 (2)	C5—H5A	1.00 (3)
Ru1—N1	2.220 (2)	C5—H5B	0.99 (3)
Ru1—Cl1	2.413 (2)	C6—N2	1.500 (3)
Ru1—Cl2	2.408 (2)	C6—H6A	0.97 (3)
C1—O1	1.133 (3)	C6—H6B	0.94 (3)
C2—O2	1.134 (3)	C7—N2	1.477 (3)
C3—N1	1.486 (3)	C7—H7A	1.00 (3)
C3—H3A	0.96 (3)	C7—H7B	1.00 (3)
C3—H3B	0.91 (3)	C7—H7C	0.99 (3)
C3—H3C	0.93 (3)	C8—N2	1.484 (3)
C4—N1	1.498 (3)	C8—H8A	0.94 (3)
C4—H4A	0.98 (4)	C8—H8B	0.97 (3)
C4—H4B	1.11 (3)	C8—H8C	0.98 (3)
C4—H4C	0.95 (4)

O1—C1—Ru1	177.3 (2)	N2—C8—H8B	114.7 (19)
O2—C2—Ru1	178.8 (2)	H8A—C8—H8B	110 (3)
N1—C3—H3A	106.0 (16)	N2—C8—H8C	108.2 (19)
N1—C3—H3B	110.6 (18)	H8A—C8—H8C	111 (3)
H3A—C3—H3B	111 (2)	H8B—C8—H8C	105 (3)
N1—C3—H3C	110.5 (19)	C1—Ru1—C2	91.90 (11)
H3A—C3—H3C	109 (3)	C1—Ru1—N2	92.33 (10)
H3B—C3—H3C	110 (3)	C2—Ru1—N2	175.71 (8)
N1—C4—H4A	111.8 (19)	C1—Ru1—N1	174.94 (8)
N1—C4—H4B	106.3 (17)	C2—Ru1—N1	93.04 (10)
H4A—C4—H4B	111 (3)	N2—Ru1—N1	82.75 (9)
N1—C4—H4C	108 (2)	C1—Ru1—Cl2	88.66 (9)
H4A—C4—H4C	112 (3)	C2—Ru1—Cl2	88.29 (9)
H4B—C4—H4C	107 (3)	N2—Ru1—Cl2	92.53 (8)
N1—C5—C6	110.6 (2)	N1—Ru1—Cl2	90.38 (8)
N1—C5—H5A	108.2 (18)	C1—Ru1—Cl1	88.62 (9)
C6—C5—H5A	109.8 (18)	C2—Ru1—Cl1	89.49 (9)
N1—C5—H5B	108.0 (18)	N2—Ru1—Cl1	89.89 (8)
C6—C5—H5B	110.0 (19)	N1—Ru1—Cl1	92.53 (8)
H5A—C5—H5B	110 (3)	Cl2—Ru1—Cl1	176.424 (19)
N2—C6—C5	110.3 (2)	C5—N1—C3	110.3 (2)
N2—C6—H6A	105.4 (18)	C5—N1—C4	108.2 (2)
C5—C6—H6A	108.6 (18)	C3—N1—C4	105.97 (18)
N2—C6—H6B	106.0 (19)	C5—N1—Ru1	104.24 (15)
C5—C6—H6B	110.2 (19)	C3—N1—Ru1	113.96 (15)
H6A—C6—H6B	116 (3)	C4—N1—Ru1	114.10 (15)
N2—C7—H7A	103.4 (18)	C7—N2—C8	106.8 (2)
N2—C7—H7B	113.4 (18)	C7—N2—C6	109.1 (2)
H7A—C7—H7B	114 (3)	C8—N2—C6	107.8 (2)
N2—C7—H7C	108.3 (19)	C7—N2—Ru1	115.10 (15)
H7A—C7—H7C	113 (2)	C8—N2—Ru1	114.35 (16)
H7B—C7—H7C	105 (2)	C6—N2—Ru1	103.38 (14)
N2—C8—H8A	107.7 (19)

N1—C5—C6—N2	−62.9 (3)	C5—C6—N2—C7	−78.1 (2)
C6—C5—N1—C3	−80.0 (2)	C5—C6—N2—C8	166.3 (2)
C6—C5—N1—C4	164.5 (2)	C5—C6—N2—Ru1	44.8 (2)
C6—C5—N1—Ru1	42.7 (2)	C1—Ru1—N2—C7	−76.26 (19)
C1—Ru1—N1—C5	−0.1 (9)	C2—Ru1—N2—C7	113.4 (10)
C2—Ru1—N1—C5	167.17 (16)	N1—Ru1—N2—C7	102.56 (18)
N2—Ru1—N1—C5	−13.63 (16)	Cl2—Ru1—N2—C7	12.49 (17)
Cl2—Ru1—N1—C5	78.87 (17)	Cl1—Ru1—N2—C7	−164.88 (17)
Cl1—Ru1—N1—C5	−103.20 (17)	C1—Ru1—N2—C8	48.00 (19)
C1—Ru1—N1—C3	120.1 (9)	C2—Ru1—N2—C8	−122.3 (10)
C2—Ru1—N1—C3	−72.57 (17)	N1—Ru1—N2—C8	−133.18 (18)
N2—Ru1—N1—C3	106.62 (16)	Cl2—Ru1—N2—C8	136.76 (17)
Cl2—Ru1—N1—C3	−160.87 (15)	Cl1—Ru1—N2—C8	−40.61 (17)
Cl1—Ru1—N1—C3	17.05 (15)	C1—Ru1—N2—C6	164.90 (16)
C1—Ru1—N1—C4	−117.9 (9)	C2—Ru1—N2—C6	−5.4 (11)
C2—Ru1—N1—C4	49.35 (19)	N1—Ru1—N2—C6	−16.28 (15)
N2—Ru1—N1—C4	−131.46 (18)	Cl2—Ru1—N2—C6	−106.34 (16)
Cl2—Ru1—N1—C4	−38.96 (17)	Cl1—Ru1—N2—C6	76.29 (16)
Cl1—Ru1—N1—C4	138.97 (17)

Experimental details

Crystal data
Chemical formula	[RuCl₂(C₆H₁₆N₂)(CO)₂]
M_r	344.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	160
a, b, c (Å)	7.463 (6), 14.579 (6), 12.718 (12)
β (°)	106.37 (8)
V (Å³)	1327.7 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.57
Crystal size (mm)	0.38 × 0.38 × 0.25

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.591, 0.69
No. of measured, independent and observed [I > 2σ(I)] reflections	3153, 2877, 2644
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.061, 1.07
No. of reflections	2877
No. of parameters	184
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.06, −0.48

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), DIRDIF99 (Beurskens et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Ru1—C1	1.872 (3)	Ru1—N1	2.220 (2)
Ru1—C2	1.872 (2)	Ru1—Cl1	2.413 (2)
Ru1—N2	2.211 (2)	Ru1—Cl2	2.408 (2)

N2—Ru1—N1	82.75 (9)

Footnotes

‡Chemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia.

Acknowledgements

The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia, for providing the research facilities.

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