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The title complex, [Cu(C14H21N2OS2)2], is isostructural with the nickel analogue, forming a square-planar coordination enviroment. The Cu atom lies on a crystallographic twofold rotation axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009397/lh2319sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009397/lh2319Isup2.hkl
Contains datablock I

CCDC reference: 600467

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.029
  • wR factor = 0.072
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C8A
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.87 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8B PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 51.00 A   3
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 26.00 From the CIF: _reflns_number_total 3133 Count of symmetry unique reflns 1782 Completeness (_total/calc) 175.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1351 Fraction of Friedel pairs measured 0.758 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 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 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: IPDS Software (Stoe & Cie, 1996); cell refinement: CELL (Burzlaff, 1996); data reduction: INTEGRATE in IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1998); software used to prepare material for publication: SHELXL97.

Bis[N,N-diisobutyl-N'-(2-thienylcarbonyl)thioureato]copper(II) top
Crystal data top
[Cu(C14H21N2OS2)2]Dx = 1.245 Mg m3
Mr = 658.44Melting point: 374.15 K
Tetragonal, I4Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I -4Cell parameters from 25 reflections
a = 13.1693 (6) Åθ = 2.0–25.9°
c = 20.2499 (16) ŵ = 0.89 mm1
V = 3512.0 (4) Å3T = 290 K
Z = 4Prismatic, green
F(000) = 13880.3 × 0.1 × 0.1 mm
Data collection top
Stoe Stadi-4
diffractometer
2938 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 26.0°, θmin = 1.9°
Profile fitted 2θ/w scans (Clegg, 1981)h = 1016
Absorption correction: ψ scan
(North et al., 1968)
k = 416
Tmin = 0.804, Tmax = 0.915l = 024
3447 measured reflections12 standard reflections every 60 min
3133 independent reflections intensity decay: none
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)] = 0.029H-atom parameters constrained
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.0341P)2 + 1.1097P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.009
3133 reflectionsΔρmax = 0.26 e Å3
184 parametersΔρmin = 0.17 e Å3
6 restraintsAbsolute structure: Flack (1983), 1665 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.007 (13)
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*/UeqOcc. (<1)
Cu10.50000.50000.837738 (19)0.04871 (11)
S10.39224 (11)0.86300 (7)0.97122 (6)0.0994 (4)
C20.4406 (2)0.7424 (2)0.96739 (15)0.0611 (7)
C30.4830 (3)0.7141 (3)1.02630 (16)0.0752 (9)
H30.51270.65111.03380.090*
C40.4765 (3)0.7908 (4)1.0738 (2)0.1058 (14)
H40.50120.78451.11670.127*
C50.4308 (4)0.8742 (4)1.0508 (2)0.1180 (18)
H50.42100.93261.07590.142*
C210.4330 (2)0.6830 (2)0.90682 (14)0.0541 (6)
O20.47946 (17)0.59874 (14)0.90685 (9)0.0655 (5)
N10.37569 (18)0.72475 (17)0.86003 (12)0.0593 (6)
C60.3662 (2)0.69167 (19)0.79794 (13)0.0540 (6)
S20.44170 (6)0.60274 (6)0.75854 (3)0.0651 (2)
N20.29335 (18)0.73776 (19)0.76307 (13)0.0647 (6)
C70.2823 (3)0.7253 (3)0.69160 (16)0.0714 (9)
H7A0.21610.75050.67850.086*0.496 (12)
H7B0.28480.65350.68110.086*0.496 (12)
H7C0.21140.71190.68200.086*0.504 (12)
H7D0.32070.66600.67820.086*0.504 (12)
C8A0.3635 (5)0.7803 (6)0.6515 (2)0.076 (3)0.496 (12)
H8A0.42970.74720.65680.091*0.496 (12)
C8B0.3163 (9)0.8146 (6)0.6499 (3)0.1390 (19)0.504 (12)
H8B0.25970.86290.64940.167*0.504 (12)
C90.3293 (5)0.7775 (5)0.57908 (18)0.1390 (19)
H9A0.37850.81170.55210.209*0.248 (6)
H9B0.26470.81080.57490.209*0.248 (6)
H9C0.32310.70820.56490.209*0.248 (6)
H9D0.26570.74210.57580.209*0.248 (6)
H9E0.37950.74300.55310.209*0.248 (6)
H9F0.32110.84560.56310.209*0.248 (6)
H9G0.34920.83330.55140.209*0.252 (6)
H9H0.26610.75000.56350.209*0.252 (6)
H9I0.38060.72580.57770.209*0.252 (6)
H9J0.31470.70610.57700.209*0.252 (6)
H9K0.39780.78930.56490.209*0.252 (6)
H9L0.28330.81360.55070.209*0.252 (6)
C10A0.3707 (15)0.8922 (7)0.6672 (7)0.1390 (6)0.496 (12)
H10A0.30410.92180.66620.209*0.248 (6)
H10B0.41310.92510.63510.209*0.248 (6)
H10C0.39960.90090.71040.209*0.248 (6)
H10D0.44040.91010.67490.209*0.248 (6)
H10E0.33150.90680.70600.209*0.248 (6)
H10F0.34490.93090.63070.209*0.248 (6)
C10B0.4060 (10)0.8705 (11)0.6788 (7)0.155 (6)0.504 (12)
H10G0.46560.82880.67550.232*0.252 (6)
H10H0.39290.88550.72440.232*0.252 (6)
H10I0.41660.93260.65500.232*0.252 (6)
H10J0.38440.93580.69450.232*0.252 (6)
H10K0.45710.87910.64550.232*0.252 (6)
H10L0.43350.83200.71490.232*0.252 (6)
C110.2244 (3)0.8096 (3)0.7971 (2)0.0849 (11)
H11A0.18970.85090.76450.102*
H11B0.26400.85450.82500.102*
C120.1449 (3)0.7538 (4)0.8398 (2)0.0997 (13)
H120.18150.70870.87000.120*
C130.0728 (4)0.6883 (5)0.7984 (3)0.1279 (18)
H13A0.11130.65030.76660.192*0.50
H13B0.02520.73130.77580.192*0.50
H13C0.03680.64240.82670.192*0.50
H13D0.00420.69900.81280.192*0.50
H13E0.09030.61800.80360.192*0.50
H13F0.07880.70690.75270.192*0.50
C140.0888 (4)0.8328 (5)0.8816 (2)0.129 (2)
H14A0.05310.79930.91670.194*0.50
H14B0.04120.86890.85440.194*0.50
H14C0.13690.87990.89990.194*0.50
H14D0.10100.89940.86390.194*0.50
H14E0.11290.82990.92630.194*0.50
H14F0.01730.81880.88080.194*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0499 (3)0.0421 (2)0.0542 (2)0.0058 (2)0.0000.000
S10.1320 (9)0.0610 (5)0.1053 (7)0.0178 (6)0.0229 (6)0.0179 (5)
C20.0635 (17)0.0502 (15)0.0697 (16)0.0036 (13)0.0114 (14)0.0085 (13)
C30.077 (2)0.081 (2)0.0682 (17)0.0094 (17)0.0004 (16)0.0112 (16)
C40.093 (3)0.145 (4)0.080 (3)0.009 (3)0.001 (2)0.038 (3)
C50.127 (4)0.103 (3)0.123 (4)0.015 (3)0.034 (3)0.060 (3)
C210.0531 (14)0.0471 (13)0.0621 (15)0.0043 (12)0.0112 (12)0.0023 (11)
O20.0862 (14)0.0510 (10)0.0592 (11)0.0224 (10)0.0057 (10)0.0036 (9)
N10.0608 (13)0.0493 (12)0.0679 (13)0.0126 (11)0.0034 (11)0.0029 (10)
C60.0544 (14)0.0462 (13)0.0615 (16)0.0038 (12)0.0008 (12)0.0087 (12)
S20.0770 (5)0.0603 (4)0.0579 (4)0.0211 (4)0.0045 (3)0.0012 (3)
N20.0563 (13)0.0632 (14)0.0745 (15)0.0131 (11)0.0013 (11)0.0182 (12)
C70.0642 (18)0.071 (2)0.078 (2)0.0036 (16)0.0155 (15)0.0189 (15)
C8A0.083 (5)0.074 (4)0.070 (4)0.009 (4)0.003 (3)0.018 (3)
C8B0.191 (5)0.149 (4)0.077 (2)0.052 (4)0.007 (3)0.017 (3)
C90.191 (5)0.149 (4)0.077 (2)0.052 (4)0.007 (3)0.017 (3)
C10A0.1908 (15)0.1494 (7)0.0769 (7)0.0524 (7)0.0069 (11)0.0174 (10)
C10B0.160 (12)0.169 (11)0.135 (10)0.113 (10)0.044 (8)0.063 (8)
C110.074 (2)0.083 (2)0.098 (3)0.0347 (19)0.0107 (19)0.028 (2)
C120.074 (2)0.123 (3)0.102 (3)0.038 (2)0.013 (2)0.039 (3)
C130.078 (3)0.151 (5)0.154 (4)0.003 (3)0.018 (3)0.026 (4)
C140.098 (3)0.191 (6)0.099 (3)0.051 (4)0.024 (3)0.018 (3)
Geometric parameters (Å, º) top
Cu1—O21.9295 (18)C9—H9F0.9600
Cu1—O2i1.9295 (18)C9—H9G0.9600
Cu1—S2i2.2342 (7)C9—H9H0.9600
Cu1—S22.2343 (7)C9—H9I0.9600
S1—C51.696 (5)C9—H9J0.9600
S1—C21.713 (3)C9—H9K0.9600
C2—C31.369 (4)C9—H9L0.9600
C2—C211.458 (4)C10A—H10A0.9600
C3—C41.397 (5)C10A—H10B0.9600
C3—H30.9300C10A—H10C0.9600
C4—C51.337 (7)C10A—H10D0.9600
C4—H40.9300C10A—H10E0.9600
C5—H50.9300C10A—H10F0.9600
C21—O21.267 (3)C10B—H10G0.9600
C21—N11.331 (4)C10B—H10H0.9600
N1—C61.337 (4)C10B—H10I0.9600
C6—N21.336 (3)C10B—H10J0.9600
C6—S21.731 (3)C10B—H10K0.9600
N2—C71.464 (4)C10B—H10L0.9600
N2—C111.482 (4)C11—C121.543 (5)
C7—C8B1.516 (5)C11—H11A0.9700
C7—C8A1.526 (4)C11—H11B0.9700
C7—H7A0.9700C12—C131.533 (7)
C7—H7B0.9700C12—C141.531 (6)
C7—H7C0.9700C12—H120.9800
C7—H7D0.9700C13—H13A0.9600
C8A—C10A1.511 (5)C13—H13B0.9600
C8A—C91.535 (4)C13—H13C0.9600
C8A—H8A0.9800C13—H13D0.9600
C8B—C10B1.510 (5)C13—H13E0.9600
C8B—C91.524 (5)C13—H13F0.9600
C8B—H8B0.9800C14—H14A0.9600
C9—H9A0.9600C14—H14B0.9600
C9—H9B0.9600C14—H14C0.9600
C9—H9C0.9600C14—H14D0.9600
C9—H9D0.9600C14—H14E0.9600
C9—H9E0.9600C14—H14F0.9600
O2—Cu1—O2i87.00 (11)H9H—C9—H9J56.3
O2—Cu1—S2i167.68 (7)H9I—C9—H9J56.3
O2i—Cu1—S2i93.69 (6)C8B—C9—H9K109.5
O2—Cu1—S293.69 (6)C8A—C9—H9K90.3
O2i—Cu1—S2167.67 (7)H9B—C9—H9K137.1
S2i—Cu1—S288.26 (4)H9C—C9—H9K98.3
C5—S1—C290.7 (2)H9D—C9—H9K151.4
C3—C2—C21127.9 (3)H9F—C9—H9K81.5
C3—C2—S1111.4 (2)H9G—C9—H9K56.3
C21—C2—S1120.7 (2)H9H—C9—H9K141.1
C2—C3—C4112.2 (4)H9I—C9—H9K56.3
C2—C3—H3123.9H9J—C9—H9K109.5
C4—C3—H3123.9C8B—C9—H9L109.5
C5—C4—C3112.4 (4)C8A—C9—H9L138.1
C5—C4—H4123.8H9A—C9—H9L81.5
C3—C4—H4123.8H9C—C9—H9L103.8
C4—C5—S1113.3 (3)H9D—C9—H9L69.6
C4—C5—H5123.4H9E—C9—H9L109.9
S1—C5—H5123.4H9G—C9—H9L56.3
O2—C21—N1129.5 (3)H9H—C9—H9L56.3
O2—C21—C2115.9 (3)H9I—C9—H9L141.1
N1—C21—C2114.6 (2)H9J—C9—H9L109.5
C21—O2—Cu1131.12 (19)H9K—C9—H9L109.5
C21—N1—C6126.1 (2)C8A—C10A—H10A109.5
N1—C6—N2114.6 (2)C8A—C10A—H10B109.5
N1—C6—S2126.9 (2)H10A—C10A—H10B109.5
N2—C6—S2118.4 (2)C8A—C10A—H10C109.5
C6—S2—Cu1106.04 (9)H10A—C10A—H10C109.5
C6—N2—C7122.9 (3)H10B—C10A—H10C109.5
C6—N2—C11118.9 (3)C8A—C10A—H10D109.5
C7—N2—C11118.1 (3)H10A—C10A—H10D141.1
N2—C7—C8B115.8 (3)H10B—C10A—H10D56.3
N2—C7—C8A113.8 (3)H10C—C10A—H10D56.3
N2—C7—H7A108.8C8A—C10A—H10E109.5
C8B—C7—H7A81.3H10A—C10A—H10E56.3
C8A—C7—H7A108.8H10B—C10A—H10E141.1
N2—C7—H7B108.8H10C—C10A—H10E56.3
C8B—C7—H7B128.6H10D—C10A—H10E109.5
C8A—C7—H7B108.8C8A—C10A—H10F109.5
H7A—C7—H7B107.7H10A—C10A—H10F56.3
N2—C7—H7C108.3H10B—C10A—H10F56.3
C8B—C7—H7C108.3H10C—C10A—H10F141.1
C8A—C7—H7C130.9H10D—C10A—H10F109.5
H7B—C7—H7C79.1H10E—C10A—H10F109.5
N2—C7—H7D108.3C8B—C10B—H10G109.5
C8B—C7—H7D108.3C8B—C10B—H10H109.5
C8A—C7—H7D82.4H10G—C10B—H10H109.5
H7A—C7—H7D131.9C8B—C10B—H10I109.5
H7C—C7—H7D107.4H10G—C10B—H10I109.5
C10A—C8A—C7113.3 (9)H10H—C10B—H10I109.5
C10A—C8A—C9104.1 (8)C8B—C10B—H10J109.5
C7—C8A—C9106.9 (4)H10G—C10B—H10J141.1
C10A—C8A—H8A110.8H10H—C10B—H10J56.3
C7—C8A—H8A110.8H10I—C10B—H10J56.3
C9—C8A—H8A110.8C8B—C10B—H10K109.5
C10B—C8B—C7113.1 (8)H10G—C10B—H10K56.3
C10B—C8B—C9115.7 (9)H10H—C10B—H10K141.1
C7—C8B—C9108.0 (5)H10I—C10B—H10K56.3
C10B—C8B—H8B106.5H10J—C10B—H10K109.5
C7—C8B—H8B106.5C8B—C10B—H10L109.5
C9—C8B—H8B106.5H10G—C10B—H10L56.3
C8B—C9—H9A117.4H10H—C10B—H10L56.3
C8A—C9—H9A109.5H10I—C10B—H10L141.1
C8B—C9—H9B80.6H10J—C10B—H10L109.5
C8A—C9—H9B109.5H10K—C10B—H10L109.5
H9A—C9—H9B109.5N2—C11—C12111.9 (3)
C8B—C9—H9C125.2N2—C11—H11A109.2
C8A—C9—H9C109.5C12—C11—H11A109.2
H9A—C9—H9C109.5N2—C11—H11B109.2
H9B—C9—H9C109.5C12—C11—H11B109.2
C8B—C9—H9D97.1H11A—C11—H11B107.9
C8A—C9—H9D109.5C13—C12—C14112.7 (4)
H9A—C9—H9D141.1C13—C12—C11112.4 (4)
H9B—C9—H9D56.3C14—C12—C11108.3 (4)
H9C—C9—H9D56.3C13—C12—H12107.7
C8B—C9—H9E138.2C14—C12—H12107.7
C8A—C9—H9E109.5C11—C12—H12107.7
H9A—C9—H9E56.3C12—C13—H13A109.5
H9B—C9—H9E141.1C12—C13—H13B109.5
H9C—C9—H9E56.3H13A—C13—H13B109.5
H9D—C9—H9E109.5C12—C13—H13C109.5
C8B—C9—H9F90.3H13A—C13—H13C109.5
C8A—C9—H9F109.5H13B—C13—H13C109.5
H9A—C9—H9F56.3C12—C13—H13D109.5
H9B—C9—H9F56.3H13A—C13—H13D141.1
H9C—C9—H9F141.1H13B—C13—H13D56.3
H9D—C9—H9F109.5H13C—C13—H13D56.3
H9E—C9—H9F109.5C12—C13—H13E109.5
C8B—C9—H9G109.5H13A—C13—H13E56.3
C8A—C9—H9G117.3H13B—C13—H13E141.1
H9B—C9—H9G80.9H13C—C13—H13E56.3
H9C—C9—H9G125.2H13D—C13—H13E109.5
H9D—C9—H9G124.8C12—C13—H13F109.5
H9E—C9—H9G81.6H13A—C13—H13F56.3
C8B—C9—H9H109.5H13B—C13—H13F56.3
C8A—C9—H9H125.3H13C—C13—H13F141.1
H9A—C9—H9H125.1H13D—C13—H13F109.5
H9B—C9—H9H51.4H13E—C13—H13F109.5
H9C—C9—H9H58.1C12—C14—H14A109.5
H9E—C9—H9H103.8C12—C14—H14B109.5
H9F—C9—H9H98.3H14A—C14—H14B109.5
H9G—C9—H9H109.5C12—C14—H14C109.5
C8B—C9—H9I109.5H14A—C14—H14C109.5
C8A—C9—H9I80.7H14B—C14—H14C109.5
H9A—C9—H9I80.9C12—C14—H14D109.5
H9B—C9—H9I160.9H14A—C14—H14D141.1
H9C—C9—H9I51.4H14B—C14—H14D56.3
H9D—C9—H9I105.5H14C—C14—H14D56.3
H9F—C9—H9I137.0C12—C14—H14E109.5
H9G—C9—H9I109.5H14A—C14—H14E56.3
H9H—C9—H9I109.5H14B—C14—H14E141.1
C8B—C9—H9J109.5H14C—C14—H14E56.3
C8A—C9—H9J97.1H14D—C14—H14E109.5
H9A—C9—H9J124.7C12—C14—H14F109.5
H9B—C9—H9J105.5H14A—C14—H14F56.3
H9D—C9—H9J49.3H14B—C14—H14F56.3
H9E—C9—H9J69.5H14C—C14—H14F141.1
H9F—C9—H9J151.4H14D—C14—H14F109.5
H9G—C9—H9J141.1H14E—C14—H14F109.5
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2ii0.932.383.264 (6)158
Symmetry code: (ii) y, x+1, z+2.
 

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