Bis­[N-phenyl­(di­cyclo­hexyl­thiophos­phinoyl)­thio­methan­amido-S,S']copper(II)

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.

Computing details

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)

Crystal data

[Cu(C19H27NPS2)2]	Z = 1
Mr = 792.60	F(000) = 419
Triclinic, P1	Dx = 1.328 Mg m^−3
a = 8.430 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.305 (3) Å	Cell parameters from 25 reflections
c = 12.380 (2) Å	θ = 11.1–12.3°
α = 89.90 (2)°	µ = 0.87 mm^−1
β = 82.31 (1)°	T = 293 K
γ = 68.62 (1)°	Prismatic, brown
V = 991.1 (3) Å^3	0.40 × 0.20 × 0.10 mm

Data collection

AFC7R diffractometer	3059 reflections with I > 2.00σ(I)
Radiation source: X-ray tube	Rint = 0.028
Graphite monochromator	θmax = 30.0°, θmin = 2.6°
ω–2θ scans	h = −11→11
Absorption correction: ψ scans (North et al., 1968)	k = −14→0
Tmin = 0.709, Tmax = 0.917	l = −17→17
6080 measured reflections	3 standard reflections every 150 reflections
5779 independent reflections	intensity decay: 0.3%

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters not refined
wR(F^2) = 0.031	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo) + 0.003|Fo|^2]
S = 1.75	(Δ/σ)max < 0.001
3059 reflections	Δρmax = 0.37 e Å^−3
214 parameters	Δρmin = −0.35 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu	0.0000	0.0000	0.0000	0.0417 (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)	0.5249	0.0235	−0.1662	0.050*
H(2)	0.2153	0.1444	−0.2470	0.066*
H(3)	0.2406	0.1684	−0.1279	0.066*
H(4)	0.2577	0.3530	−0.2349	0.090*
H(5)	0.4278	0.2793	−0.1877	0.090*
H(6)	0.3771	0.2383	−0.4001	0.103*
H(7)	0.4960	0.3119	−0.3674	0.103*
H(8)	0.6527	0.0866	−0.4366	0.087*
H(9)	0.6828	0.1076	−0.3180	0.087*
H(10)	0.6421	−0.1010	−0.3310	0.068*
H(11)	0.4698	−0.0275	−0.3760	0.068*
H(12)	0.6103	−0.3063	−0.2565	0.047*
H(13)	0.7551	−0.2096	−0.1560	0.070*
H(14)	0.6904	−0.2674	−0.0503	0.070*
H(15)	0.9200	−0.4337	−0.2252	0.093*
H(16)	0.9699	−0.4143	−0.1118	0.093*
H(17)	0.9333	−0.6270	−0.1282	0.095*
H(18)	0.8048	−0.5334	−0.0325	0.095*
H(19)	0.7213	−0.5693	−0.2380	0.078*
H(20)	0.6573	−0.6268	−0.1319	0.078*
H(21)	0.4901	−0.4049	−0.0645	0.062*
H(22)	0.4430	−0.4256	−0.1784	0.062*
H(23)	0.0018	−0.0688	−0.4010	0.072*
H(24)	−0.1242	−0.1415	−0.5334	0.087*
H(25)	−0.0134	−0.3665	−0.6040	0.091*
H(26)	0.2363	−0.5242	−0.5488	0.090*
H(27)	0.3669	−0.4538	−0.4198	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0317 (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)

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)	0.95	C(12)—C(13)	1.513 (5)
C(3)—C(4)	1.530 (5)	C(12)—H(19)	0.95
C(3)—H(2)	0.95	C(12)—H(20)	0.95
C(3)—H(3)	0.95	C(13)—H(21)	0.95
C(4)—C(5)	1.504 (6)	C(13)—H(22)	0.95
C(4)—H(4)	0.95	C(14)—C(15)	1.381 (4)
C(4)—H(5)	0.95	C(14)—C(19)	1.376 (5)
C(5)—C(6)	1.490 (6)	C(15)—C(16)	1.387 (5)
C(5)—H(6)	0.95	C(15)—H(23)	0.95
C(5)—H(7)	0.95	C(16)—C(17)	1.342 (6)
C(6)—C(7)	1.530 (5)	C(16)—H(24)	0.95
C(6)—H(8)	0.95	C(17)—C(18)	1.374 (6)
C(6)—H(9)	0.95	C(17)—H(25)	0.95
C(7)—H(10)	0.95	C(18)—C(19)	1.370 (5)
C(7)—H(11)	0.95	C(18)—H(26)	0.95
C(8)—C(9)	1.533 (4)	C(19)—H(27)	0.95
S(1)···C(9)^i	3.834 (4)	C(12)···C(18)^vi	3.949 (6)
S(2)···C(2)^ii	3.878 (3)	C(12)···C(13)^vii	4.000 (5)
C(5)···C(19)^iii	3.803 (6)	C(13)···C(13)^vii	3.917 (7)
C(5)···C(19)^iv	3.958 (6)	C(15)···C(15)^viii	3.629 (9)
C(6)···C(15)^v	3.763 (5)	C(15)···C(16)^viii	3.800 (6)
C(6)···C(16)^v	3.819 (6)	C(17)···C(18)^ix	3.614 (6)
C(6)···C(15)^iv	3.854 (6)	C(17)···C(17)^ix	3.84 (1)
C(6)···C(14)^iv	3.863 (5)	C(18)···C(18)^ix	3.896 (9)
C(7)···C(16)^v	3.839 (5)	C(19)···C(19)^vi	3.861 (8)
C(12)···C(17)^vi	3.887 (6)
S(1)—Cu—S(1)	180.00	P(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)^x	84.15 (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)^x	95.85 (4)	C(9)—C(8)—H(12)	107.5
S(2)—Cu—S(2)	180.00	C(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)	106.2	C(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)	106.3	C(12)—C(11)—H(18)	109.2
C(7)—C(2)—H(1)	106.3	H(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)	109.2	C(11)—C(12)—H(19)	109.1
C(2)—C(3)—H(3)	109.1	C(11)—C(12)—H(20)	108.9
C(4)—C(3)—H(2)	109.3	C(13)—C(12)—H(19)	108.8
C(4)—C(3)—H(3)	109.2	C(13)—C(12)—H(20)	108.7
H(2)—C(3)—H(3)	109.6	H(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)	109.1	C(8)—C(13)—H(21)	109.0
C(3)—C(4)—H(5)	109.2	C(8)—C(13)—H(22)	109.1
C(5)—C(4)—H(4)	108.9	C(12)—C(13)—H(21)	109.1
C(5)—C(4)—H(5)	109.0	C(12)—C(13)—H(22)	109.1
H(4)—C(4)—H(5)	109.5	H(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)	108.7	N(1)—C(14)—C(19)	116.7 (3)
C(4)—C(5)—H(7)	108.7	C(15)—C(14)—C(19)	118.2 (3)
C(6)—C(5)—H(6)	108.8	C(14)—C(15)—C(16)	119.6 (4)
C(6)—C(5)—H(7)	108.9	C(14)—C(15)—H(23)	120.3
H(6)—C(5)—H(7)	109.5	C(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)	108.9	C(15)—C(16)—H(24)	119.3
C(5)—C(6)—H(9)	108.8	C(17)—C(16)—H(24)	119.2
C(7)—C(6)—H(8)	109.0	C(16)—C(17)—C(18)	119.6 (4)
C(7)—C(6)—H(9)	108.9	C(16)—C(17)—H(25)	120.2
H(8)—C(6)—H(9)	109.4	C(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)	109.3	C(17)—C(18)—H(26)	120.0
C(2)—C(7)—H(11)	109.4	C(19)—C(18)—H(26)	120.3
C(6)—C(7)—H(10)	109.3	C(14)—C(19)—C(18)	121.4 (4)
C(6)—C(7)—H(11)	109.3	C(14)—C(19)—H(27)	119.3
H(10)—C(7)—H(11)	109.4	C(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) x−1, y, z; (ii) −x+1, −y, −z; (iii) x, y+1, z; (iv) −x+1, −y, −z−1; (v) x+1, y, z; (vi) −x+1, −y−1, −z−1; (vii) −x+1, −y−1, −z; (viii) −x, −y, −z−1; (ix) −x, −y−1, −z−1; (x) −x, −y, −z.