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The ligands in [Cu(C19H27NPS2)2] adopt an S,S'-chelation mode leading to an S4 donor set which defines a square-planar geometry about the Cu atom, which lies on an inversion centre.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100011586/ta1299sup1.cif
Contains datablocks ehorn01, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011586/ta1299Isup2.hkl
Contains datablock I

CCDC reference: 153877

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN for Windows; software used to prepare material for publication: TEXSAN for Windows.

(I) top
Crystal data top
[Cu(C19H27NPS2)2]Z = 1
Mr = 792.60F(000) = 419
Triclinic, P1Dx = 1.328 Mg m3
a = 8.430 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.305 (3) ÅCell parameters from 25 reflections
c = 12.380 (2) Åθ = 11.1–12.3°
α = 89.90 (2)°µ = 0.87 mm1
β = 82.31 (1)°T = 293 K
γ = 68.62 (1)°Prismatic, brown
V = 991.1 (3) Å30.40 × 0.20 × 0.10 mm
Data collection top
AFC7R
diffractometer
3059 reflections with I > 2.00σ(I)
Radiation source: X-ray tubeRint = 0.028
Graphite monochromatorθmax = 30.0°, θmin = 2.6°
ω–2θ scansh = 1111
Absorption correction: ψ scans
(North et al., 1968)
k = 140
Tmin = 0.709, Tmax = 0.917l = 1717
6080 measured reflections3 standard reflections every 150 reflections
5779 independent reflections intensity decay: 0.3%
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.044H-atom parameters not refined
wR(F2) = 0.031Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.003|Fo|2]
S = 1.75(Δ/σ)max < 0.001
3059 reflectionsΔρmax = 0.37 e Å3
214 parametersΔρmin = 0.35 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu0.00000.00000.00000.0417 (1)
S(1)0.01127 (9)0.0680 (1)0.17644 (6)0.0702 (3)
S(2)0.29323 (8)0.09424 (8)0.00246 (6)0.0501 (2)
P(1)0.38695 (8)0.13057 (7)0.15628 (6)0.0368 (2)
N(1)0.2918 (2)0.2211 (2)0.3221 (2)0.0405 (6)
C(1)0.2240 (3)0.1472 (3)0.2338 (2)0.0388 (7)
C(2)0.4473 (3)0.0120 (3)0.2109 (2)0.0420 (8)
C(3)0.2950 (3)0.1501 (3)0.2015 (3)0.0554 (9)
C(4)0.3552 (4)0.2690 (3)0.2368 (3)0.075 (1)
C(5)0.4533 (4)0.2396 (4)0.3504 (3)0.086 (1)
C(6)0.6010 (4)0.1033 (3)0.3623 (3)0.073 (1)
C(7)0.5438 (4)0.0174 (3)0.3278 (2)0.057 (1)
C(8)0.5741 (3)0.2922 (3)0.1800 (2)0.0388 (7)
C(9)0.7247 (3)0.2841 (3)0.1269 (3)0.059 (1)
C(10)0.8809 (4)0.4202 (4)0.1489 (3)0.077 (1)
C(11)0.8358 (4)0.5436 (4)0.1096 (3)0.079 (1)
C(12)0.6868 (4)0.5521 (3)0.1614 (3)0.065 (1)
C(13)0.5305 (3)0.4183 (3)0.1406 (2)0.0517 (9)
C(14)0.1968 (3)0.2554 (3)0.3954 (2)0.0406 (8)
C(15)0.0507 (4)0.1623 (3)0.4305 (2)0.060 (1)
C(16)0.0242 (4)0.2061 (4)0.5091 (3)0.072 (1)
C(17)0.0413 (4)0.3379 (4)0.5515 (3)0.076 (1)
C(18)0.1881 (5)0.4311 (3)0.5185 (3)0.075 (1)
C(19)0.2647 (4)0.3892 (3)0.4417 (2)0.058 (1)
H(1)0.52490.02350.16620.050*
H(2)0.21530.14440.24700.066*
H(3)0.24060.16840.12790.066*
H(4)0.25770.35300.23490.090*
H(5)0.42780.27930.18770.090*
H(6)0.37710.23830.40010.103*
H(7)0.49600.31190.36740.103*
H(8)0.65270.08660.43660.087*
H(9)0.68280.10760.31800.087*
H(10)0.64210.10100.33100.068*
H(11)0.46980.02750.37600.068*
H(12)0.61030.30630.25650.047*
H(13)0.75510.20960.15600.070*
H(14)0.69040.26740.05030.070*
H(15)0.92000.43370.22520.093*
H(16)0.96990.41430.11180.093*
H(17)0.93330.62700.12820.095*
H(18)0.80480.53340.03250.095*
H(19)0.72130.56930.23800.078*
H(20)0.65730.62680.13190.078*
H(21)0.49010.40490.06450.062*
H(22)0.44300.42560.17840.062*
H(23)0.00180.06880.40100.072*
H(24)0.12420.14150.53340.087*
H(25)0.01340.36650.60400.091*
H(26)0.23630.52420.54880.090*
H(27)0.36690.45380.41980.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.0317 (2)0.0561 (4)0.0385 (3)0.0191 (2)0.0000 (2)0.0067 (2)
S(1)0.0311 (4)0.1278 (8)0.0494 (5)0.0289 (5)0.0014 (3)0.0320 (5)
S(2)0.0351 (4)0.0711 (6)0.0366 (4)0.0103 (4)0.0057 (3)0.0041 (4)
P(1)0.0290 (3)0.0423 (4)0.0377 (4)0.0114 (3)0.0057 (3)0.0010 (3)
N(1)0.034 (1)0.047 (1)0.038 (1)0.011 (1)0.0074 (9)0.003 (1)
C(1)0.029 (1)0.052 (2)0.038 (1)0.017 (1)0.005 (1)0.003 (1)
C(2)0.032 (1)0.044 (2)0.054 (2)0.017 (1)0.011 (1)0.004 (1)
C(3)0.040 (2)0.043 (2)0.076 (2)0.008 (1)0.007 (1)0.005 (2)
C(4)0.055 (2)0.039 (2)0.123 (3)0.008 (2)0.012 (2)0.014 (2)
C(5)0.063 (2)0.060 (2)0.138 (4)0.025 (2)0.014 (2)0.048 (2)
C(6)0.056 (2)0.065 (2)0.091 (3)0.020 (2)0.005 (2)0.030 (2)
C(7)0.050 (2)0.053 (2)0.060 (2)0.015 (2)0.005 (1)0.008 (2)
C(8)0.033 (1)0.035 (2)0.043 (2)0.007 (1)0.002 (1)0.002 (1)
C(9)0.038 (2)0.055 (2)0.082 (2)0.012 (1)0.021 (2)0.003 (2)
C(10)0.035 (2)0.066 (2)0.120 (3)0.002 (2)0.023 (2)0.001 (2)
C(11)0.058 (2)0.060 (2)0.099 (3)0.005 (2)0.018 (2)0.014 (2)
C(12)0.073 (2)0.043 (2)0.070 (2)0.014 (2)0.000 (2)0.010 (2)
C(13)0.051 (2)0.049 (2)0.054 (2)0.017 (1)0.010 (1)0.009 (1)
C(14)0.039 (1)0.049 (2)0.033 (1)0.017 (1)0.002 (1)0.002 (1)
C(15)0.050 (2)0.064 (2)0.053 (2)0.004 (2)0.012 (1)0.013 (2)
C(16)0.046 (2)0.098 (3)0.062 (2)0.011 (2)0.019 (2)0.018 (2)
C(17)0.068 (2)0.112 (3)0.060 (2)0.046 (2)0.014 (2)0.018 (2)
C(18)0.096 (3)0.063 (2)0.069 (2)0.031 (2)0.014 (2)0.018 (2)
C(19)0.066 (2)0.050 (2)0.053 (2)0.010 (2)0.018 (2)0.001 (2)
Geometric parameters (Å, º) top
Cu—S(1)2.274 (1)C(8)—C(13)1.537 (5)
Cu—S(2)2.307 (1)C(8)—H(12)0.95
S(1)—C(1)1.726 (3)C(9)—C(10)1.528 (5)
S(2)—P(1)1.999 (1)C(9)—H(13)0.95
P(1)—C(1)1.834 (3)C(9)—H(14)0.95
P(1)—C(2)1.823 (4)C(10)—C(11)1.516 (6)
P(1)—C(8)1.820 (3)C(10)—H(15)0.95
N(1)—C(1)1.272 (4)C(10)—H(16)0.95
N(1)—C(14)1.412 (4)C(11)—C(12)1.515 (5)
C(2)—C(3)1.522 (5)C(11)—H(17)0.95
C(2)—C(7)1.534 (5)C(11)—H(18)0.95
C(2)—H(1)0.95C(12)—C(13)1.513 (5)
C(3)—C(4)1.530 (5)C(12)—H(19)0.95
C(3)—H(2)0.95C(12)—H(20)0.95
C(3)—H(3)0.95C(13)—H(21)0.95
C(4)—C(5)1.504 (6)C(13)—H(22)0.95
C(4)—H(4)0.95C(14)—C(15)1.381 (4)
C(4)—H(5)0.95C(14)—C(19)1.376 (5)
C(5)—C(6)1.490 (6)C(15)—C(16)1.387 (5)
C(5)—H(6)0.95C(15)—H(23)0.95
C(5)—H(7)0.95C(16)—C(17)1.342 (6)
C(6)—C(7)1.530 (5)C(16)—H(24)0.95
C(6)—H(8)0.95C(17)—C(18)1.374 (6)
C(6)—H(9)0.95C(17)—H(25)0.95
C(7)—H(10)0.95C(18)—C(19)1.370 (5)
C(7)—H(11)0.95C(18)—H(26)0.95
C(8)—C(9)1.533 (4)C(19)—H(27)0.95
S(1)···C(9)i3.834 (4)C(12)···C(18)vi3.949 (6)
S(2)···C(2)ii3.878 (3)C(12)···C(13)vii4.000 (5)
C(5)···C(19)iii3.803 (6)C(13)···C(13)vii3.917 (7)
C(5)···C(19)iv3.958 (6)C(15)···C(15)viii3.629 (9)
C(6)···C(15)v3.763 (5)C(15)···C(16)viii3.800 (6)
C(6)···C(16)v3.819 (6)C(17)···C(18)ix3.614 (6)
C(6)···C(15)iv3.854 (6)C(17)···C(17)ix3.84 (1)
C(6)···C(14)iv3.863 (5)C(18)···C(18)ix3.896 (9)
C(7)···C(16)v3.839 (5)C(19)···C(19)vi3.861 (8)
C(12)···C(17)vi3.887 (6)
S(1)—Cu—S(1)180.00P(1)—C(8)—C(9)111.8 (2)
S(1)—Cu—S(2)95.85 (4)P(1)—C(8)—C(13)111.7 (2)
S(1)—Cu—S(2)x84.15 (4)P(1)—C(8)—H(12)107.6
S(1)x—Cu—S(2)84.15 (4)C(9)—C(8)—C(13)110.3 (3)
S(1)x—Cu—S(2)x95.85 (4)C(9)—C(8)—H(12)107.5
S(2)—Cu—S(2)180.00C(13)—C(8)—H(12)107.6
Cu—S(1)—C(1)109.0 (1)C(8)—C(9)—C(10)110.9 (3)
Cu—S(2)—P(1)102.47 (5)C(8)—C(9)—H(13)109.2
S(2)—P(1)—C(1)110.2 (1)C(8)—C(9)—H(14)109.0
S(2)—P(1)—C(2)111.3 (1)C(10)—C(9)—H(13)109.4
S(2)—P(1)—C(8)111.1 (1)C(10)—C(9)—H(14)109.1
C(1)—P(1)—C(2)107.6 (2)H(13)—C(9)—H(14)109.3
C(1)—P(1)—C(8)107.6 (2)C(9)—C(10)—C(11)111.1 (3)
C(2)—P(1)—C(8)108.8 (2)C(9)—C(10)—H(15)109.0
C(1)—N(1)—C(14)123.9 (3)C(9)—C(10)—H(16)109.2
S(1)—C(1)—P(1)117.1 (2)C(11)—C(10)—H(15)109.1
S(1)—C(1)—N(1)131.0 (3)C(11)—C(10)—H(16)109.2
P(1)—C(1)—N(1)111.9 (2)H(15)—C(10)—H(16)109.3
P(1)—C(2)—C(3)112.4 (2)C(10)—C(11)—C(12)111.0 (4)
P(1)—C(2)—C(7)114.3 (3)C(10)—C(11)—H(17)109.1
P(1)—C(2)—H(1)106.2C(10)—C(11)—H(18)109.0
C(3)—C(2)—C(7)110.6 (3)C(12)—C(11)—H(17)109.1
C(3)—C(2)—H(1)106.3C(12)—C(11)—H(18)109.2
C(7)—C(2)—H(1)106.3H(17)—C(11)—H(18)109.4
C(2)—C(3)—C(4)110.5 (3)C(11)—C(12)—C(13)111.7 (3)
C(2)—C(3)—H(2)109.2C(11)—C(12)—H(19)109.1
C(2)—C(3)—H(3)109.1C(11)—C(12)—H(20)108.9
C(4)—C(3)—H(2)109.3C(13)—C(12)—H(19)108.8
C(4)—C(3)—H(3)109.2C(13)—C(12)—H(20)108.7
H(2)—C(3)—H(3)109.6H(19)—C(12)—H(20)109.6
C(3)—C(4)—C(5)111.2 (4)C(8)—C(13)—C(12)111.1 (3)
C(3)—C(4)—H(4)109.1C(8)—C(13)—H(21)109.0
C(3)—C(4)—H(5)109.2C(8)—C(13)—H(22)109.1
C(5)—C(4)—H(4)108.9C(12)—C(13)—H(21)109.1
C(5)—C(4)—H(5)109.0C(12)—C(13)—H(22)109.1
H(4)—C(4)—H(5)109.5H(21)—C(13)—H(22)109.4
C(4)—C(5)—C(6)112.4 (4)N(1)—C(14)—C(15)124.9 (3)
C(4)—C(5)—H(6)108.7N(1)—C(14)—C(19)116.7 (3)
C(4)—C(5)—H(7)108.7C(15)—C(14)—C(19)118.2 (3)
C(6)—C(5)—H(6)108.8C(14)—C(15)—C(16)119.6 (4)
C(6)—C(5)—H(7)108.9C(14)—C(15)—H(23)120.3
H(6)—C(5)—H(7)109.5C(16)—C(15)—H(23)120.1
C(5)—C(6)—C(7)111.8 (3)C(15)—C(16)—C(17)121.5 (4)
C(5)—C(6)—H(8)108.9C(15)—C(16)—H(24)119.3
C(5)—C(6)—H(9)108.8C(17)—C(16)—H(24)119.2
C(7)—C(6)—H(8)109.0C(16)—C(17)—C(18)119.6 (4)
C(7)—C(6)—H(9)108.9C(16)—C(17)—H(25)120.2
H(8)—C(6)—H(9)109.4C(18)—C(17)—H(25)120.2
C(2)—C(7)—C(6)110.1 (3)C(17)—C(18)—C(19)119.7 (4)
C(2)—C(7)—H(10)109.3C(17)—C(18)—H(26)120.0
C(2)—C(7)—H(11)109.4C(19)—C(18)—H(26)120.3
C(6)—C(7)—H(10)109.3C(14)—C(19)—C(18)121.4 (4)
C(6)—C(7)—H(11)109.3C(14)—C(19)—H(27)119.3
H(10)—C(7)—H(11)109.4C(18)—C(19)—H(27)119.2
Cu—S(1)—C(1)—P(1)11.3 (2)C(1)—P(1)—C(2)—C(7)67.5 (3)
Cu—S(1)—C(1)—N(1)166.4 (3)C(1)—P(1)—C(8)—C(9)174.8 (2)
Cu—S(2)—P(1)—C(1)23.2 (1)C(1)—P(1)—C(8)—C(13)61.0 (3)
Cu—S(2)—P(1)—C(2)96.0 (1)C(1)—N(1)—C(14)—C(15)45.8 (6)
Cu—S(2)—P(1)—C(8)142.5 (1)C(1)—N(1)—C(14)—C(19)139.9 (4)
S(1)—Cu—S(1)—C(1)142.5 (1)C(2)—P(1)—C(8)—C(9)58.5 (3)
S(1)—Cu—S(2)—P(1)15.15 (6)C(2)—P(1)—C(8)—C(13)177.4 (2)
S(1)—C(1)—P(1)—S(2)23.8 (2)C(2)—C(3)—C(4)—C(5)55.8 (5)
S(1)—C(1)—P(1)—C(2)97.7 (2)C(2)—C(7)—C(6)—C(5)55.3 (5)
S(1)—C(1)—P(1)—C(8)145.2 (2)C(3)—C(2)—P(1)—C(8)176.1 (3)
S(1)—C(1)—N(1)—C(14)0.3 (6)C(3)—C(2)—C(7)—C(6)56.4 (4)
S(2)—Cu—S(1)—C(1)3.7 (1)C(3)—C(4)—C(5)—C(6)55.1 (5)
S(2)—Cu—S(2)—P(1)176.3 (1)C(4)—C(3)—C(2)—C(7)57.0 (4)
S(2)—P(1)—C(1)—N(1)154.3 (2)C(4)—C(5)—C(6)—C(7)55.1 (5)
S(2)—P(1)—C(2)—C(3)61.0 (3)C(7)—C(2)—P(1)—C(8)48.9 (3)
S(2)—P(1)—C(2)—C(7)171.7 (2)C(8)—C(9)—C(10)—C(11)56.5 (5)
S(2)—P(1)—C(8)—C(9)64.5 (3)C(8)—C(13)—C(12)—C(11)55.8 (5)
S(2)—P(1)—C(8)—C(13)59.7 (3)C(9)—C(8)—C(13)—C(12)55.4 (4)
P(1)—C(1)—N(1)—C(14)177.5 (3)C(9)—C(10)—C(11)—C(12)56.2 (5)
P(1)—C(2)—C(3)—C(4)173.8 (3)C(10)—C(9)—C(8)—C(13)55.7 (4)
P(1)—C(2)—C(7)—C(6)175.4 (3)C(10)—C(11)—C(12)—C(13)56.2 (5)
P(1)—C(8)—C(9)—C(10)179.4 (3)C(14)—C(15)—C(16)—C(17)0.5 (7)
P(1)—C(8)—C(13)—C(12)179.6 (3)C(14)—C(19)—C(18)—C(17)0.7 (7)
N(1)—C(1)—P(1)—C(2)84.2 (3)C(15)—C(14)—C(19)—C(18)1.7 (7)
N(1)—C(1)—P(1)—C(8)33.0 (3)C(15)—C(16)—C(17)—C(18)1.5 (8)
N(1)—C(14)—C(15)—C(16)175.2 (4)C(16)—C(15)—C(14)—C(19)1.1 (6)
N(1)—C(14)—C(19)—C(18)176.3 (4)C(16)—C(17)—C(18)—C(19)0.8 (8)
C(1)—P(1)—C(2)—C(3)59.8 (3)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x, y+1, z; (iv) x+1, y, z1; (v) x+1, y, z; (vi) x+1, y1, z1; (vii) x+1, y1, z; (viii) x, y, z1; (ix) x, y1, z1; (x) x, y, z.
 

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