Literature DB >> 21754305

Tris(ethyl-enediamine)-cobalt(III) diformatodioxalatoindate(III) dihydrate.

Juying Tong, Qinhe Pan.   

Abstract

In the cation of the title compound, [Co(C(2)H(8)N(2))(3)][In(C(2)O(4))(2)(CHO(2))(2)]·2H(2)O, the Co-N bond lengths lie in the range 1.960 (5)-1.997 (5) Å. In the anion, the In(III) atom is coordin-ated by four O atoms from two oxalato ligands and two O atoms from two formato ligands in a distorted octa-hedral geometry. Inter-molecular O-H⋯O and N-H⋯O hydrogen bonds form an extensive hydrogen-bonding network, which link the cations, anions and water mol-ecules into three-dimensional structure.

Entities:  

Year:  2011        PMID: 21754305      PMCID: PMC3089116          DOI: 10.1107/S1600536811013109

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For related structures, see: Chen et al. (2005 ▶); Du et al. (2004 ▶); Pan et al. (2005 ▶, 2008 ▶, 2010a ▶,b ▶, 2011 ▶); Stalder & Wilkinson (1997 ▶); Wang et al. (2003a ▶,b ▶,c ▶, 2004 ▶); Yu et al. (2001 ▶); Zhang et al. (2003a ▶,b ▶).

Experimental

Crystal data

[Co(C2H8N2)3][In(C2O4)2(CHO2)2]·2H2O M = 656.17 Triclinic, a = 8.2048 (16) Å b = 12.016 (2) Å c = 12.052 (2) Å α = 79.09 (3)° β = 81.45 (3)° γ = 88.43 (3)° V = 1153.7 (4) Å3 Z = 2 Mo Kα radiation μ = 1.80 mm−1 T = 293 K 0.2 × 0.18 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002 ▶) T min = 0.686, T max = 1 12132 measured reflections 5263 independent reflections 3963 reflections with I > 2σ(I) R int = 0.084

Refinement

R[F 2 > 2σ(F 2)] = 0.060 wR(F 2) = 0.168 S = 1.05 5263 reflections 311 parameters H-atom parameters constrained Δρmax = 1.01 e Å−3 Δρmin = −1.13 e Å−3 Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013109/cv5068sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013109/cv5068Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Co(C2H8N2)3][In(CHO2)2(C2O4)2]·2H2OZ = 2
Mr = 656.17F(000) = 664
Triclinic, P1Dx = 1.889 Mg m3
a = 8.2048 (16) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.016 (2) ÅCell parameters from 11095 reflections
c = 12.052 (2) Åθ = 3.1–27.5°
α = 79.09 (3)°µ = 1.80 mm1
β = 81.45 (3)°T = 293 K
γ = 88.43 (3)°Block, yellow
V = 1153.7 (4) Å30.2 × 0.18 × 0.15 mm
Rigaku R-AXIS RAPID-S diffractometer5263 independent reflections
Radiation source: fine-focus sealed tube3963 reflections with I > 2σ(I)
graphiteRint = 0.084
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)h = −10→10
Tmin = 0.686, Tmax = 1k = −15→15
12132 measured reflectionsl = −15→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0731P)2 + 0.3428P] where P = (Fo2 + 2Fc2)/3
5263 reflections(Δ/σ)max = 0.002
311 parametersΔρmax = 1.01 e Å3
0 restraintsΔρmin = −1.13 e Å3
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.
xyzUiso*/Ueq
In10.74015 (5)0.84824 (3)0.22384 (3)0.03043 (16)
Co10.91881 (8)0.71299 (6)0.70020 (6)0.02243 (19)
O10.7451 (5)0.7212 (3)0.3813 (3)0.0322 (9)
O20.7964 (6)0.5351 (3)0.4313 (3)0.0427 (11)
O30.6793 (5)0.6899 (3)0.1777 (3)0.0311 (9)
O40.7309 (5)0.5043 (3)0.2225 (3)0.0332 (9)
O50.4826 (5)0.8852 (4)0.2719 (4)0.0393 (10)
O60.3200 (5)1.0247 (4)0.3203 (4)0.0456 (11)
O70.7497 (5)0.9860 (3)0.3147 (4)0.0343 (9)
O80.5935 (5)1.1319 (4)0.3600 (4)0.0507 (12)
O91.0041 (5)0.8544 (4)0.1954 (4)0.0500 (12)
O101.0526 (6)0.6669 (4)0.2194 (4)0.0539 (13)
O110.7412 (7)0.9122 (5)0.0455 (4)0.0629 (15)
O120.6375 (8)1.0792 (5)0.0718 (5)0.0687 (16)
N10.9683 (6)0.8481 (4)0.7639 (4)0.0351 (12)
H1A1.04300.89270.71410.080*
H1B0.87600.88870.77690.080*
N20.9620 (6)0.6240 (5)0.8484 (4)0.0360 (12)
H2A0.88270.57140.87490.080*
H2B1.05920.58800.83880.080*
N30.6829 (6)0.7226 (4)0.7557 (4)0.0343 (11)
H3A0.66470.70270.83240.080*
H3B0.64740.79410.73620.080*
N40.8610 (6)0.5716 (4)0.6530 (4)0.0336 (11)
H4A0.87040.58270.57640.080*
H4B0.93140.51620.67590.080*
N51.1499 (6)0.7020 (4)0.6257 (4)0.0307 (11)
H5A1.21640.74330.65520.080*
H5B1.18370.62940.63830.080*
N60.8846 (6)0.8113 (4)0.5550 (4)0.0342 (11)
H6A0.82900.77320.51510.080*
H6B0.82450.87220.56920.080*
C11.0354 (12)0.8056 (8)0.8742 (6)0.072 (3)
H1C1.15430.79860.85820.080*
H1D1.01090.86040.92410.080*
C20.9658 (11)0.6976 (7)0.9314 (7)0.067 (2)
H2C0.85480.70810.96880.080*
H2D1.03150.66290.98930.080*
C30.5917 (7)0.6445 (6)0.7038 (6)0.0427 (16)
H3C0.57840.67950.62620.080*
H3D0.48320.62830.74770.080*
C40.6898 (7)0.5366 (5)0.7039 (5)0.0371 (14)
H4C0.68720.49460.78130.080*
H4D0.64520.48920.65900.080*
C51.1587 (7)0.7451 (5)0.5007 (5)0.0359 (14)
H5C1.12130.68750.46370.080*
H5D1.27110.76560.46670.080*
C61.0470 (8)0.8487 (5)0.4871 (5)0.0369 (14)
H6C1.09170.90980.51570.080*
H6D1.03600.87490.40740.080*
C70.7596 (7)0.6186 (5)0.3633 (5)0.0296 (12)
C80.7208 (6)0.6011 (4)0.2445 (4)0.0235 (11)
C90.4559 (7)0.9783 (5)0.3048 (5)0.0351 (14)
C100.6120 (7)1.0395 (5)0.3296 (5)0.0351 (14)
C111.0973 (8)0.7662 (7)0.2032 (6)0.0447 (16)
H11A1.21000.77890.19570.080*
C120.6927 (10)1.0096 (7)0.0090 (7)0.057 (2)
H12A0.69741.0326−0.06960.080*
O2W0.5103 (6)0.2921 (4)0.0086 (4)0.0538 (15)
H2WA0.4820.2861−0.0280.080*
H2WB0.5310.2510.0300.080*
O1W0.7148 (6)0.4807 (5)−0.0054 (4)0.0612 (16)
H1WA0.6680.422−0.00170.080*
H1WB0.68900.48820.0600.080*
U11U22U33U12U13U23
In10.0318 (3)0.0236 (3)0.0380 (3)0.00444 (17)−0.01046 (18)−0.00754 (18)
Co10.0216 (4)0.0219 (4)0.0252 (4)0.0017 (3)−0.0058 (3)−0.0063 (3)
O10.042 (2)0.025 (2)0.031 (2)0.0068 (18)−0.0109 (18)−0.0073 (17)
O20.068 (3)0.030 (2)0.031 (2)0.011 (2)−0.019 (2)0.0007 (18)
O30.043 (2)0.022 (2)0.032 (2)0.0033 (18)−0.0167 (18)−0.0064 (17)
O40.043 (2)0.021 (2)0.037 (2)−0.0027 (18)−0.0084 (18)−0.0067 (17)
O50.027 (2)0.030 (2)0.066 (3)0.0050 (18)−0.013 (2)−0.020 (2)
O60.030 (2)0.035 (2)0.075 (3)0.0086 (19)−0.007 (2)−0.019 (2)
O70.028 (2)0.025 (2)0.052 (3)0.0011 (17)−0.0104 (18)−0.0103 (19)
O80.045 (3)0.038 (3)0.082 (4)0.006 (2)−0.019 (2)−0.037 (3)
O90.029 (2)0.051 (3)0.065 (3)0.003 (2)−0.001 (2)−0.002 (2)
O100.044 (3)0.050 (3)0.064 (3)0.008 (2)−0.001 (2)−0.008 (3)
O110.080 (4)0.052 (3)0.049 (3)0.007 (3)−0.019 (3)0.015 (3)
O120.094 (4)0.049 (3)0.066 (4)−0.001 (3)−0.037 (3)0.002 (3)
N10.029 (3)0.037 (3)0.044 (3)0.000 (2)−0.006 (2)−0.019 (2)
N20.036 (3)0.043 (3)0.031 (3)0.003 (2)−0.009 (2)−0.009 (2)
N30.032 (3)0.033 (3)0.041 (3)0.001 (2)−0.007 (2)−0.012 (2)
N40.034 (3)0.032 (3)0.037 (3)0.002 (2)−0.008 (2)−0.008 (2)
N50.028 (2)0.026 (3)0.037 (3)0.003 (2)−0.004 (2)−0.007 (2)
N60.039 (3)0.024 (3)0.040 (3)0.003 (2)−0.013 (2)−0.004 (2)
C10.111 (7)0.073 (6)0.038 (4)−0.031 (5)−0.019 (4)−0.012 (4)
C20.097 (7)0.065 (5)0.050 (5)0.013 (5)−0.037 (4)−0.024 (4)
C30.029 (3)0.051 (4)0.053 (4)−0.009 (3)−0.010 (3)−0.017 (3)
C40.034 (3)0.034 (3)0.042 (4)−0.007 (3)−0.002 (3)−0.006 (3)
C50.039 (3)0.034 (3)0.033 (3)−0.001 (3)−0.002 (3)−0.002 (3)
C60.045 (4)0.032 (3)0.031 (3)−0.006 (3)−0.003 (3)−0.001 (3)
C70.033 (3)0.025 (3)0.032 (3)0.005 (2)−0.007 (2)−0.008 (2)
C80.026 (3)0.023 (3)0.022 (3)−0.001 (2)−0.006 (2)−0.005 (2)
C90.030 (3)0.030 (3)0.048 (4)0.002 (3)−0.008 (3)−0.013 (3)
C100.030 (3)0.028 (3)0.048 (4)−0.001 (3)−0.012 (3)−0.005 (3)
C110.027 (3)0.056 (5)0.046 (4)0.007 (3)−0.003 (3)0.001 (3)
C120.057 (5)0.060 (5)0.046 (4)−0.008 (4)−0.015 (4)0.012 (4)
O2W0.076 (4)0.049 (3)0.046 (3)0.009 (3)−0.028 (2)−0.018 (2)
O1W0.066 (3)0.078 (4)0.038 (3)−0.022 (3)0.005 (2)−0.013 (3)
In1—O112.140 (5)N4—C41.485 (7)
In1—O92.143 (4)N4—H4A0.9000
In1—O72.160 (4)N4—H4B0.9000
In1—O52.164 (4)N5—C51.489 (8)
In1—O32.171 (4)N5—H5A0.9000
In1—O12.203 (4)N5—H5B0.9000
Co1—N31.960 (5)N6—C61.489 (8)
Co1—N61.970 (5)N6—H6A0.9000
Co1—N21.976 (5)N6—H6B0.9000
Co1—N41.981 (5)C1—C21.439 (11)
Co1—N51.986 (5)C1—H1C0.9700
Co1—N11.997 (5)C1—H1D0.9700
O1—C71.292 (7)C2—H2C0.9700
O2—C71.230 (7)C2—H2D0.9700
O3—C81.280 (6)C3—C41.507 (9)
O4—C81.239 (6)C3—H3C0.9700
O5—C91.259 (7)C3—H3D0.9700
O6—C91.238 (7)C4—H4C0.9700
O7—C101.290 (7)C4—H4D0.9700
O8—C101.232 (7)C5—C61.524 (8)
O9—C111.286 (8)C5—H5C0.9700
O10—C111.229 (8)C5—H5D0.9700
O11—C121.247 (9)C6—H6C0.9700
O12—C121.262 (10)C6—H6D0.9700
N1—C11.509 (9)C7—C81.565 (7)
N1—H1A0.9000C9—C101.587 (8)
N1—H1B0.9000C11—H11A0.9300
N2—C21.459 (9)C12—H12A0.9300
N2—H2A0.9000O2W—H2WA0.5459
N2—H2B0.9000O2W—H2WB0.5460
N3—C31.493 (8)O1W—H1WA0.8043
N3—H3A0.9000O1W—H1WB0.8031
N3—H3B0.9000
O11—In1—O988.9 (2)Co1—N5—H5B109.9
O11—In1—O7110.48 (19)H5A—N5—H5B108.3
O9—In1—O786.65 (17)C6—N6—Co1109.6 (4)
O11—In1—O594.8 (2)C6—N6—H6A109.8
O9—In1—O5163.60 (18)Co1—N6—H6A109.8
O7—In1—O577.07 (15)C6—N6—H6B109.8
O11—In1—O382.94 (18)Co1—N6—H6B109.8
O9—In1—O3104.71 (18)H6A—N6—H6B108.2
O7—In1—O3162.86 (16)C2—C1—N1111.7 (6)
O5—In1—O391.61 (16)C2—C1—H1C109.3
O11—In1—O1157.73 (19)N1—C1—H1C109.3
O9—In1—O190.38 (17)C2—C1—H1D109.3
O7—In1—O191.69 (15)N1—C1—H1D109.3
O5—In1—O192.12 (16)H1C—C1—H1D107.9
O3—In1—O175.71 (14)C1—C2—N2109.6 (6)
N3—Co1—N689.5 (2)C1—C2—H2C109.8
N3—Co1—N291.9 (2)N2—C2—H2C109.8
N6—Co1—N2175.7 (2)C1—C2—H2D109.8
N3—Co1—N485.3 (2)N2—C2—H2D109.8
N6—Co1—N494.4 (2)H2C—C2—H2D108.2
N2—Co1—N489.8 (2)N3—C3—C4108.0 (5)
N3—Co1—N5173.0 (2)N3—C3—H3C110.1
N6—Co1—N585.1 (2)C4—C3—H3C110.1
N2—Co1—N593.7 (2)N3—C3—H3D110.1
N4—Co1—N590.6 (2)C4—C3—H3D110.1
N3—Co1—N191.9 (2)H3C—C3—H3D108.4
N6—Co1—N190.6 (2)N4—C4—C3106.1 (5)
N2—Co1—N185.3 (2)N4—C4—H4C110.5
N4—Co1—N1174.2 (2)C3—C4—H4C110.5
N5—Co1—N192.7 (2)N4—C4—H4D110.5
C7—O1—In1113.2 (3)C3—C4—H4D110.5
C8—O3—In1114.3 (3)H4C—C4—H4D108.7
C9—O5—In1114.6 (4)N5—C5—C6106.6 (5)
C10—O7—In1113.9 (4)N5—C5—H5C110.4
C11—O9—In1124.1 (5)C6—C5—H5C110.4
C12—O11—In1122.2 (5)N5—C5—H5D110.4
C1—N1—Co1107.6 (4)C6—C5—H5D110.4
C1—N1—H1A110.2H5C—C5—H5D108.6
Co1—N1—H1A110.2N6—C6—C5105.9 (5)
C1—N1—H1B110.2N6—C6—H6C110.6
Co1—N1—H1B110.2C5—C6—H6C110.6
H1A—N1—H1B108.5N6—C6—H6D110.6
C2—N2—Co1110.7 (4)C5—C6—H6D110.6
C2—N2—H2A109.5H6C—C6—H6D108.7
Co1—N2—H2A109.5O2—C7—O1126.1 (5)
C2—N2—H2B109.5O2—C7—C8118.4 (5)
Co1—N2—H2B109.5O1—C7—C8115.5 (5)
H2A—N2—H2B108.1O4—C8—O3125.3 (5)
C3—N3—Co1108.8 (4)O4—C8—C7118.6 (5)
C3—N3—H3A109.9O3—C8—C7116.1 (4)
Co1—N3—H3A109.9O6—C9—O5125.9 (6)
C3—N3—H3B109.9O6—C9—C10118.0 (5)
Co1—N3—H3B109.9O5—C9—C10116.1 (5)
H3A—N3—H3B108.3O8—C10—O7125.8 (5)
C4—N4—Co1110.4 (4)O8—C10—C9118.9 (5)
C4—N4—H4A109.6O7—C10—C9115.3 (5)
Co1—N4—H4A109.6O10—C11—O9126.7 (6)
C4—N4—H4B109.6O10—C11—H11A116.7
Co1—N4—H4B109.6O9—C11—H11A116.7
H4A—N4—H4B108.1O11—C12—O12124.2 (7)
C5—N5—Co1109.0 (4)O11—C12—H12A117.9
C5—N5—H5A109.9O12—C12—H12A117.9
Co1—N5—H5A109.9H2WA—O2W—H2WB109.4
C5—N5—H5B109.9H1WA—O1W—H1WB98.5
D—H···AD—HH···AD···AD—H···A
N1—H1A···O7i0.902.223.019 (7)148
N1—H1B···O6ii0.902.252.981 (7)139
N2—H2A···O1Wiii0.902.022.857 (7)155
N2—H2B···O4iv0.902.143.017 (6)166
N3—H3A···O2Wv0.902.233.017 (7)146
N3—H3B···O6ii0.902.173.002 (7)154
N3—H3B···O8ii0.902.503.153 (7)130
N4—H4A···O20.902.112.915 (6)148
N4—H4B···O10iv0.902.333.102 (7)144
N4—H4B···O2iv0.902.533.166 (7)128
N5—H5A···O8i0.902.162.986 (6)153
N5—H5B···O4iv0.902.273.022 (6)141
N5—H5B···O2iv0.902.283.060 (6)145
N6—H6A···O10.902.052.917 (7)161
N6—H6B···O6ii0.902.193.024 (7)154
O2W—H2WA···O3vi0.552.362.889 (6)163
O2W—H2WB···O12vii0.552.222.751 (7)166
O1W—H1WA···O2W0.802.032.821 (7)169
O1W—H1WB···O40.802.092.836 (6)156
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
N1—H1A⋯O7i0.902.223.019 (7)148
N1—H1B⋯O6ii0.902.252.981 (7)139
N2—H2A⋯O1Wiii0.902.022.857 (7)155
N2—H2B⋯O4iv0.902.143.017 (6)166
N3—H3A⋯O2Wv0.902.233.017 (7)146
N3—H3B⋯O6ii0.902.173.002 (7)154
N3—H3B⋯O8ii0.902.503.153 (7)130
N4—H4A⋯O20.902.112.915 (6)148
N4—H4B⋯O10iv0.902.333.102 (7)144
N4—H4B⋯O2iv0.902.533.166 (7)128
N5—H5A⋯O8i0.902.162.986 (6)153
N5—H5B⋯O4iv0.902.273.022 (6)141
N5—H5B⋯O2iv0.902.283.060 (6)145
N6—H6A⋯O10.902.052.917 (7)161
N6—H6B⋯O6ii0.902.193.024 (7)154
O2W—H2WA⋯O3vi0.552.362.889 (6)163
O2W—H2WB⋯O12vii0.552.222.751 (7)166
O1W—H1WA⋯O2W0.802.032.821 (7)169
O1W—H1WB⋯O40.802.092.836 (6)156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

  4 in total

1.  [Ge(7)O(13)(OH)(2)F(3)](3)(-).Cl(-).2[Ni(dien)(2)](2+): the first chainlike germanate templated by a transition metal complex.

Authors:  Hong-Xia Zhang; Jie Zhang; Shou-Tian Zheng; Guo-Yu Yang
Journal:  Inorg Chem       Date:  2003-10-20       Impact factor: 5.165

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  [[Zn2(HPO4)4][Co(dien)2]].H3O: a zinc phosphate with multidirectional intersecting helical channels.

Authors:  Yu Wang; Jihong Yu; Min Guo; Ruren Xu
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-05       Impact factor: 15.336

4.  Chirality transfer from guest chiral metal complexes to inorganic framework: the role of hydrogen bonding.

Authors:  Yu Wang; Jihong Yu; Yi Li; Zhan Shi; Ruren Xu
Journal:  Chemistry       Date:  2003-10-17       Impact factor: 5.236

  4 in total
  4 in total

1.  Bis(diethyl-enetriamine)-cobalt(III) hexa-chloridoindate(III).

Authors:  Qihui Wu; Shangwen Chen; Cailing Zhang; Xia Zhi; Zelin Chen
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-05-07

2.  Tris(2,2'-bi-1H-imidazole-κN,N)cobalt(II) hydrogen phosphate.

Authors:  Zhiqiang Liang; Fuxiang Wang; Qihui Wu; Xia Zhi; Qinhe Pan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-09-17

3.  Tris(ethyl-enediamine-κN,N')cobalt(III) aqua-tris-(oxalato-κO,O)indate(III).

Authors:  Zhe Zhang; Fuxiang Wang; Shuangquan Liao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-17

4.  Bis[hexa-amminecobalt(III)] penta-chloride nitrate.

Authors:  Qihui Wu; Chunyu Du; Yang Lv; Guoliang Chen; Qinhe Pan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-05-16
  4 in total

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