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The title compound, [Cu2(C6H7N3S2)2(C2H3N)2](BF4)2, is a dimer with a central Cu2S2 core resulting from thio­semi­carbazone sulfur bridging. Both Cu–TCT units (TCT is the thio­phene-2-carboxaldehyde thio­semicarbazone anion) are roughly planar and are parallel to one another and perpendicular to the Cu2S2 plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001887/om6281sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001887/om6281Isup2.hkl
Contains datablock I

CCDC reference: 298511

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](Wave) = 0.000 Å
  • R factor = 0.045
  • wR factor = 0.111
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

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Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 69.45 From the CIF: _reflns_number_total 4947 Count of symmetry unique reflns 2689 Completeness (_total/calc) 183.97% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2258 Fraction of Friedel pairs measured 0.840 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: XSHELL (Bruker, 2004); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Bis(µ-thiophene-2-carboxaldehyde thiosemicarbazonato)bis[acetonitrilecopper(I)] bis(tetrafluoroborate) top
Crystal data top
[Cu2(C6H7N3S2)2(C2H3N)2](BF4)2F(000) = 1504
Mr = 753.34Dx = 1.792 Mg m3
Orthorhombic, Pca21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2acCell parameters from 470 reflections
a = 13.3357 (3) Åθ = 3.9–69.5°
b = 9.1867 (2) ŵ = 5.40 mm1
c = 22.7980 (5) ÅT = 100 K
V = 2793.01 (11) Å3Block, yellow
Z = 40.12 × 0.10 × 0.10 mm
Data collection top
Bruker SMART APEX-II CCD area-detector
diffractometer
4947 independent reflections
Radiation source: fine-focus sealed tube3981 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.088
ω and φ scansθmax = 69.5°, θmin = 3.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1514
Tmin = 0.534, Tmax = 0.583k = 1010
30209 measured reflectionsl = 2726
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0722P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
4947 reflectionsΔρmax = 1.22 e Å3
363 parametersΔρmin = 0.36 e Å3
1 restraintAbsolute structure: Flack (1983), with 2291 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.13 (4)
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
xyzUiso*/Ueq
Cu10.39792 (8)0.09495 (11)0.67287 (5)0.0278 (3)
Cu20.32874 (8)0.37145 (11)0.63921 (5)0.0281 (3)
S10.45720 (14)0.21886 (19)0.59090 (8)0.0267 (4)
S20.27153 (13)0.24911 (19)0.72134 (8)0.0255 (4)
S30.28958 (15)0.1596 (2)0.74389 (9)0.0303 (4)
S40.44232 (18)0.6218 (2)0.56496 (9)0.0379 (5)
N10.3724 (5)0.1753 (8)0.4880 (3)0.0349 (16)
H1A0.33240.13210.46410.042*
H1B0.41000.24510.47580.042*
N20.3162 (5)0.0259 (7)0.5602 (3)0.0256 (14)
H20.27880.01440.53410.031*
N30.3119 (5)0.0244 (6)0.6173 (3)0.0229 (13)
N40.3645 (5)0.2891 (7)0.8235 (3)0.0302 (15)
H4A0.40700.33150.84610.036*
H4B0.32880.21810.83650.036*
N50.4128 (5)0.4452 (7)0.7521 (3)0.0248 (14)
H50.44990.48740.77790.030*
N60.4153 (5)0.4943 (6)0.6947 (3)0.0264 (14)
N70.4880 (5)0.0443 (7)0.7367 (3)0.0274 (14)
N80.2442 (5)0.4299 (7)0.5747 (3)0.0314 (15)
C10.3762 (6)0.1342 (8)0.5442 (3)0.0242 (16)
C20.2515 (6)0.1335 (7)0.6239 (3)0.0251 (16)
H2A0.21690.16640.59110.030*
C30.2344 (6)0.2071 (8)0.6788 (3)0.0287 (16)
C40.1741 (5)0.3303 (8)0.6851 (3)0.0233 (16)
H40.13760.37250.65470.028*
C50.1753 (6)0.3827 (8)0.7431 (4)0.0306 (17)
H5A0.13990.46460.75510.037*
C60.2331 (6)0.3022 (8)0.7800 (4)0.0330 (18)
H60.24120.32170.81970.040*
C70.3539 (6)0.3331 (8)0.7687 (3)0.0255 (17)
C80.4722 (5)0.6086 (7)0.6873 (3)0.0228 (16)
H80.50430.64670.72010.027*
C90.4885 (5)0.6793 (7)0.6321 (3)0.0241 (16)
C100.5493 (5)0.8116 (7)0.6269 (3)0.0173 (14)
H100.58150.86090.65710.021*
C110.5495 (6)0.8502 (8)0.5656 (4)0.0313 (18)
H110.58340.93160.55170.038*
C120.4984 (6)0.7628 (8)0.5303 (4)0.0325 (18)
H120.49370.77770.49010.039*
C130.5329 (6)0.0154 (9)0.7766 (4)0.0309 (18)
C140.5885 (7)0.0250 (11)0.8299 (4)0.040 (2)
H14A0.54500.07740.85600.060*
H14B0.61230.06150.84900.060*
H14C0.64450.08540.81950.060*
C150.2093 (6)0.4684 (9)0.5318 (4)0.0309 (18)
C160.1690 (8)0.5187 (13)0.4765 (4)0.062 (3)
H16A0.15470.43660.45190.092*
H16B0.21720.58040.45750.092*
H16C0.10840.57240.48340.092*
B10.6568 (7)0.0400 (11)0.4220 (4)0.032 (2)
B20.4270 (8)0.4732 (14)0.3819 (5)0.046 (3)
F10.5652 (4)0.0146 (8)0.4346 (3)0.073 (2)
F20.6961 (5)0.1020 (5)0.4733 (2)0.0566 (16)
F30.6508 (5)0.1390 (7)0.3785 (3)0.0639 (17)
F40.7217 (4)0.0727 (6)0.4063 (3)0.0579 (16)
F50.3290 (4)0.4519 (8)0.3738 (3)0.0684 (18)
F60.4819 (5)0.4017 (6)0.3376 (3)0.072 (2)
F70.4545 (5)0.4194 (8)0.4359 (3)0.092 (3)
F80.4519 (4)0.6199 (6)0.3802 (3)0.0572 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0333 (6)0.0288 (6)0.0213 (5)0.0024 (4)0.0042 (5)0.0007 (5)
Cu20.0325 (6)0.0286 (6)0.0232 (6)0.0024 (5)0.0035 (5)0.0003 (5)
S10.0266 (10)0.0275 (9)0.0261 (10)0.0011 (7)0.0009 (8)0.0006 (8)
S20.0249 (9)0.0283 (9)0.0235 (9)0.0035 (7)0.0008 (8)0.0004 (7)
S30.0349 (11)0.0292 (10)0.0267 (10)0.0048 (8)0.0003 (8)0.0005 (8)
S40.0464 (13)0.0367 (12)0.0305 (11)0.0060 (9)0.0005 (9)0.0057 (9)
N10.043 (4)0.040 (4)0.022 (4)0.009 (3)0.006 (3)0.005 (3)
N20.035 (4)0.026 (3)0.016 (3)0.005 (3)0.002 (3)0.003 (2)
N30.031 (3)0.023 (3)0.015 (3)0.002 (3)0.003 (2)0.002 (2)
N40.035 (4)0.038 (4)0.018 (3)0.008 (3)0.002 (3)0.004 (3)
N50.026 (3)0.029 (3)0.019 (3)0.004 (2)0.000 (2)0.002 (3)
N60.034 (4)0.025 (3)0.020 (3)0.001 (3)0.001 (3)0.003 (3)
N70.033 (4)0.023 (3)0.026 (4)0.000 (3)0.003 (3)0.004 (3)
N80.032 (4)0.033 (4)0.030 (4)0.004 (3)0.001 (3)0.002 (3)
C10.024 (4)0.026 (4)0.023 (4)0.004 (3)0.000 (3)0.001 (3)
C20.025 (4)0.023 (4)0.028 (4)0.002 (3)0.001 (3)0.010 (3)
C30.027 (4)0.038 (4)0.021 (4)0.003 (3)0.001 (3)0.001 (3)
C40.023 (4)0.023 (4)0.024 (4)0.005 (3)0.002 (3)0.005 (3)
C50.027 (4)0.030 (4)0.035 (5)0.003 (3)0.003 (4)0.004 (3)
C60.040 (5)0.028 (4)0.031 (5)0.004 (3)0.001 (4)0.001 (3)
C70.027 (4)0.024 (4)0.025 (4)0.004 (3)0.002 (3)0.002 (3)
C80.026 (4)0.022 (4)0.021 (4)0.002 (3)0.000 (3)0.004 (3)
C90.024 (4)0.023 (4)0.026 (4)0.004 (3)0.004 (3)0.002 (3)
C100.011 (3)0.020 (3)0.021 (4)0.006 (2)0.004 (3)0.003 (3)
C110.025 (4)0.020 (4)0.049 (5)0.003 (3)0.013 (4)0.007 (3)
C120.032 (5)0.034 (4)0.032 (4)0.002 (3)0.000 (4)0.008 (4)
C130.028 (4)0.035 (4)0.030 (5)0.001 (3)0.002 (4)0.001 (4)
C140.042 (6)0.056 (6)0.023 (5)0.011 (4)0.005 (4)0.005 (4)
C150.031 (5)0.039 (5)0.023 (4)0.004 (3)0.001 (3)0.004 (4)
C160.063 (7)0.075 (8)0.047 (7)0.003 (6)0.019 (5)0.023 (6)
B10.037 (5)0.039 (5)0.019 (5)0.006 (4)0.001 (4)0.003 (4)
B20.047 (7)0.067 (8)0.024 (5)0.015 (5)0.003 (4)0.011 (5)
F10.039 (3)0.112 (5)0.068 (4)0.008 (3)0.007 (3)0.051 (4)
F20.093 (5)0.044 (3)0.033 (3)0.018 (3)0.024 (3)0.009 (2)
F30.077 (4)0.077 (4)0.038 (3)0.015 (3)0.012 (3)0.021 (3)
F40.048 (4)0.068 (3)0.057 (4)0.018 (3)0.011 (3)0.029 (3)
F50.053 (4)0.094 (5)0.059 (4)0.021 (3)0.011 (3)0.005 (3)
F60.081 (5)0.053 (3)0.082 (5)0.004 (3)0.035 (4)0.027 (3)
F70.091 (5)0.126 (6)0.059 (4)0.071 (5)0.038 (4)0.048 (4)
F80.060 (4)0.061 (4)0.051 (3)0.018 (3)0.013 (3)0.004 (3)
Geometric parameters (Å, º) top
Cu1—N71.944 (7)C2—H2A0.9300
Cu1—N32.031 (6)C3—C41.396 (11)
Cu1—S12.327 (2)C4—C51.408 (11)
Cu1—S22.463 (2)C4—H40.9300
Cu1—Cu22.8094 (15)C5—C61.359 (11)
Cu2—N81.929 (7)C5—H5A0.9300
Cu2—N62.051 (6)C6—H60.9300
Cu2—S22.313 (2)C8—C91.432 (10)
Cu2—S12.472 (2)C8—H80.9300
S1—C11.705 (8)C9—C101.466 (10)
S2—C71.723 (8)C10—C111.441 (11)
S3—C31.712 (8)C10—H100.9300
S3—C61.720 (8)C11—C121.325 (12)
S4—C121.691 (8)C11—H110.9300
S4—C91.733 (8)C12—H120.9300
N1—C11.336 (10)C13—C141.472 (11)
N1—H1A0.8600C14—H14A0.9600
N1—H1B0.8600C14—H14B0.9600
N2—C11.327 (9)C14—H14C0.9600
N2—N31.384 (8)C15—C161.445 (12)
N2—H20.8600C16—H16A0.9600
N3—C21.294 (9)C16—H16B0.9600
N4—C71.319 (10)C16—H16C0.9600
N4—H4A0.8600B1—F31.347 (11)
N4—H4B0.8600B1—F11.352 (11)
N5—C71.350 (10)B1—F41.396 (11)
N5—N61.385 (8)B1—F21.402 (11)
N5—H50.8600B2—F51.335 (12)
N6—C81.307 (9)B2—F71.377 (12)
N7—C131.120 (10)B2—F81.388 (13)
N8—C151.140 (10)B2—F61.409 (14)
C2—C31.442 (11)
N7—Cu1—N3133.4 (2)C4—C3—S3111.5 (6)
N7—Cu1—S1120.6 (2)C2—C3—S3124.4 (6)
N3—Cu1—S187.43 (18)C3—C4—C5111.4 (7)
N7—Cu1—S2103.00 (19)C3—C4—H4124.3
N3—Cu1—S2101.75 (18)C5—C4—H4124.3
S1—Cu1—S2108.15 (7)C6—C5—C4113.7 (7)
N7—Cu1—Cu2128.62 (19)C6—C5—H5A123.1
N3—Cu1—Cu297.60 (17)C4—C5—H5A123.1
S1—Cu1—Cu256.62 (6)C5—C6—S3111.5 (6)
S2—Cu1—Cu251.53 (5)C5—C6—H6124.3
N8—Cu2—N6130.2 (3)S3—C6—H6124.3
N8—Cu2—S2124.0 (2)N4—C7—N5116.0 (7)
N6—Cu2—S287.36 (18)N4—C7—S2121.6 (6)
N8—Cu2—S1102.9 (2)N5—C7—S2122.4 (6)
N6—Cu2—S1101.33 (18)N6—C8—C9124.4 (7)
S2—Cu2—S1108.27 (7)N6—C8—H8117.8
N8—Cu2—Cu1130.7 (2)C9—C8—H8117.8
N6—Cu2—Cu198.28 (17)C8—C9—C10122.1 (7)
S2—Cu2—Cu156.49 (5)C8—C9—S4125.7 (5)
S1—Cu2—Cu151.79 (5)C10—C9—S4112.2 (5)
C1—S1—Cu193.6 (3)C11—C10—C9106.5 (6)
C1—S1—Cu295.6 (3)C11—C10—H10126.7
Cu1—S1—Cu271.59 (6)C9—C10—H10126.7
C7—S2—Cu294.6 (3)C12—C11—C10116.0 (7)
C7—S2—Cu195.9 (3)C12—C11—H11122.0
Cu2—S2—Cu171.98 (6)C10—C11—H11122.0
C3—S3—C691.9 (4)C11—C12—S4114.1 (6)
C12—S4—C991.2 (4)C11—C12—H12122.9
C1—N1—H1A120.0S4—C12—H12122.9
C1—N1—H1B120.0N7—C13—C14177.8 (9)
H1A—N1—H1B120.0C13—C14—H14A109.5
C1—N2—N3122.3 (6)C13—C14—H14B109.5
C1—N2—H2118.9H14A—C14—H14B109.5
N3—N2—H2118.9C13—C14—H14C109.5
C2—N3—N2113.2 (6)H14A—C14—H14C109.5
C2—N3—Cu1134.2 (5)H14B—C14—H14C109.5
N2—N3—Cu1112.5 (4)N8—C15—C16177.7 (9)
C7—N4—H4A120.0C15—C16—H16A109.5
C7—N4—H4B120.0C15—C16—H16B109.5
H4A—N4—H4B120.0H16A—C16—H16B109.5
C7—N5—N6121.9 (6)C15—C16—H16C109.5
C7—N5—H5119.1H16A—C16—H16C109.5
N6—N5—H5119.1H16B—C16—H16C109.5
C8—N6—N5113.4 (6)F3—B1—F1110.7 (8)
C8—N6—Cu2133.6 (5)F3—B1—F4110.4 (8)
N5—N6—Cu2113.0 (4)F1—B1—F4109.8 (8)
C13—N7—Cu1174.0 (6)F3—B1—F2111.2 (8)
C15—N8—Cu2168.3 (7)F1—B1—F2108.2 (8)
N2—C1—N1116.9 (7)F4—B1—F2106.5 (7)
N2—C1—S1123.5 (6)F5—B2—F7109.4 (9)
N1—C1—S1119.6 (6)F5—B2—F8111.8 (10)
N3—C2—C3124.2 (7)F7—B2—F8108.1 (9)
N3—C2—H2A117.9F5—B2—F6109.9 (9)
C3—C2—H2A117.9F7—B2—F6109.6 (10)
C4—C3—C2124.1 (7)F8—B2—F6108.0 (8)
N7—Cu1—Cu2—N8177.1 (4)C7—N5—N6—Cu23.7 (9)
N3—Cu1—Cu2—N89.4 (3)N8—Cu2—N6—C839.2 (8)
S1—Cu1—Cu2—N872.5 (3)S2—Cu2—N6—C8173.2 (7)
S2—Cu1—Cu2—N8108.4 (3)S1—Cu2—N6—C878.7 (7)
N7—Cu1—Cu2—N66.7 (3)Cu1—Cu2—N6—C8131.2 (7)
N3—Cu1—Cu2—N6179.8 (3)N8—Cu2—N6—N5140.8 (5)
S1—Cu1—Cu2—N697.93 (18)S2—Cu2—N6—N56.8 (5)
S2—Cu1—Cu2—N681.24 (19)S1—Cu2—N6—N5101.3 (5)
N7—Cu1—Cu2—S274.5 (3)Cu1—Cu2—N6—N548.7 (5)
N3—Cu1—Cu2—S299.00 (18)N3—Cu1—N7—C1388 (6)
S1—Cu1—Cu2—S2179.17 (9)S1—Cu1—N7—C13153 (6)
N7—Cu1—Cu2—S1104.7 (3)S2—Cu1—N7—C1333 (6)
N3—Cu1—Cu2—S181.83 (18)Cu2—Cu1—N7—C1383 (6)
S2—Cu1—Cu2—S1179.17 (9)N6—Cu2—N8—C1573 (3)
N7—Cu1—S1—C1146.7 (3)S2—Cu2—N8—C15167 (3)
N3—Cu1—S1—C16.1 (3)S1—Cu2—N8—C1544 (3)
S2—Cu1—S1—C195.4 (3)Cu1—Cu2—N8—C1594 (3)
Cu2—Cu1—S1—C194.7 (2)N3—N2—C1—N1178.7 (6)
N7—Cu1—S1—Cu2118.6 (2)N3—N2—C1—S12.4 (10)
N3—Cu1—S1—Cu2100.84 (17)Cu1—S1—C1—N26.4 (6)
S2—Cu1—S1—Cu20.68 (8)Cu2—S1—C1—N278.3 (6)
N8—Cu2—S1—C140.2 (3)Cu1—S1—C1—N1174.6 (6)
N6—Cu2—S1—C1176.4 (3)Cu2—S1—C1—N1102.8 (6)
S2—Cu2—S1—C192.7 (3)N2—N3—C2—C3179.2 (6)
Cu1—Cu2—S1—C192.0 (3)Cu1—N3—C2—C33.7 (12)
N8—Cu2—S1—Cu1132.1 (2)N3—C2—C3—C4175.8 (7)
N6—Cu2—S1—Cu191.68 (18)N3—C2—C3—S31.2 (11)
S2—Cu2—S1—Cu10.73 (8)C6—S3—C3—C40.1 (6)
N8—Cu2—S2—C7145.5 (3)C6—S3—C3—C2177.5 (7)
N6—Cu2—S2—C77.0 (3)C2—C3—C4—C5177.0 (7)
S1—Cu2—S2—C794.0 (3)S3—C3—C4—C50.3 (8)
Cu1—Cu2—S2—C794.7 (3)C3—C4—C5—C60.7 (10)
N8—Cu2—S2—Cu1119.8 (2)C4—C5—C6—S30.8 (9)
N6—Cu2—S2—Cu1101.74 (17)C3—S3—C6—C50.5 (6)
S1—Cu2—S2—Cu10.68 (8)N6—N5—C7—N4174.6 (7)
N7—Cu1—S2—C736.5 (3)N6—N5—C7—S24.0 (10)
N3—Cu1—S2—C7176.7 (3)Cu2—S2—C7—N4170.5 (6)
S1—Cu1—S2—C792.2 (3)Cu1—S2—C7—N498.2 (6)
Cu2—Cu1—S2—C792.9 (3)Cu2—S2—C7—N58.0 (7)
N7—Cu1—S2—Cu2129.4 (2)Cu1—S2—C7—N580.3 (6)
N3—Cu1—S2—Cu290.42 (17)N5—N6—C8—C9179.2 (6)
S1—Cu1—S2—Cu20.73 (8)Cu2—N6—C8—C90.8 (11)
C1—N2—N3—C2177.9 (7)N6—C8—C9—C10177.0 (6)
C1—N2—N3—Cu14.3 (8)N6—C8—C9—S43.8 (11)
N7—Cu1—N3—C245.3 (8)C12—S4—C9—C8179.5 (7)
S1—Cu1—N3—C2176.4 (7)C12—S4—C9—C100.2 (5)
S2—Cu1—N3—C275.6 (7)C8—C9—C10—C11179.6 (6)
Cu2—Cu1—N3—C2127.8 (7)S4—C9—C10—C110.3 (7)
N7—Cu1—N3—N2137.6 (5)C9—C10—C11—C120.2 (9)
S1—Cu1—N3—N26.5 (4)C10—C11—C12—S40.1 (10)
S2—Cu1—N3—N2101.5 (4)C9—S4—C12—C110.0 (7)
Cu2—Cu1—N3—N249.4 (5)Cu1—N7—C13—C1427 (28)
C7—N5—N6—C8176.4 (7)Cu2—N8—C15—C167 (27)
 

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