Redetermination of bis­(O,O'-dicyclo­hexyl phospho­rodithio­ato)nickel(II)

The structure of the title compound, [Ni(C₁₂H₂₂O₂PS₂)₂], has been determined previously [Chichang et al. (1987). Chin. J. Struct. Chem. 6, 186], but the current determination provides a significant increase in the precision of the geometric parameters. The Ni^II atom lies on a crystallographic center of symmetry in a distorted square-planar coodination environment.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.032
• wR factor = 0.084
• Data-to-parameter ratio = 23.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       5.32 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   S1      ..       8.74 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   S2      ..       7.24 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Ni1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

bis(O,O'-dicyclohexyl phosphorodithioato)nickel(II)

Crystal data

[Ni(C12H22O2PS2)2]	F(000) = 684
Mr = 645.50	Dx = 1.376 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 21951 reflections
a = 11.7991 (6) Å	θ = 2.1–27.9°
b = 9.3550 (5) Å	µ = 1.02 mm^−1
c = 14.2138 (8) Å	T = 296 K
β = 96.764 (5)°	Hexagonal-shaped plate, violet
V = 1558.01 (14) Å^3	0.58 × 0.48 × 0.07 mm
Z = 2

Data collection

Stoe IPDS-2 diffractometer	3706 independent reflections
Radiation source: fine-focus sealed tube	2749 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 6.67 pixels mm^-1	θmax = 27.9°, θmin = 2.1°
rotation method; ω? φ? scans	h = −15→15
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.589, Tmax = 0.932	l = −18→18
20380 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0384P)^2 + 0.2064P] where P = (Fo^2 + 2Fc^2)/3
3706 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.21810 (19)	0.5006 (2)	0.66142 (17)	0.0655 (5)
H1	0.2860	0.5574	0.6530	0.079*
C2	0.1139 (2)	0.5839 (3)	0.6311 (2)	0.0883 (8)
H2A	0.1117	0.6075	0.5644	0.106*
H2B	0.1160	0.6727	0.6665	0.106*
C3	0.0086 (2)	0.5027 (3)	0.6463 (3)	0.1050 (11)
H3A	−0.0577	0.5630	0.6300	0.126*
H3B	0.0014	0.4201	0.6048	0.126*
C4	0.0115 (3)	0.4550 (4)	0.7459 (3)	0.1259 (15)
H4A	−0.0556	0.3974	0.7523	0.151*
H4B	0.0091	0.5379	0.7866	0.151*
C5	0.1164 (4)	0.3693 (4)	0.77762 (19)	0.1111 (12)
H5A	0.1137	0.2798	0.7430	0.133*
H5B	0.1184	0.3473	0.8445	0.133*
C6	0.2236 (3)	0.4508 (3)	0.76115 (18)	0.0891 (8)
H6A	0.2326	0.5326	0.8034	0.107*
H6B	0.2896	0.3894	0.7757	0.107*
C7	0.2784 (2)	0.1288 (2)	0.40608 (15)	0.0681 (6)
H7	0.3486	0.1726	0.3889	0.082*
C8	0.1875 (3)	0.1352 (3)	0.32420 (17)	0.0922 (8)
H8A	0.2155	0.0922	0.2693	0.111*
H8B	0.1695	0.2344	0.3092	0.111*
C9	0.0801 (3)	0.0582 (5)	0.3448 (2)	0.1152 (11)
H9A	0.0463	0.1089	0.3941	0.138*
H9B	0.0253	0.0579	0.2883	0.138*
C10	0.1054 (4)	−0.0924 (4)	0.3759 (3)	0.1401 (15)
H10A	0.1323	−0.1458	0.3243	0.168*
H10B	0.0362	−0.1376	0.3917	0.168*
C11	0.1945 (4)	−0.0957 (3)	0.4605 (3)	0.1175 (12)
H11A	0.2120	−0.1942	0.4779	0.141*
H11B	0.1647	−0.0497	0.5137	0.141*
C12	0.3022 (3)	−0.0208 (3)	0.4404 (2)	0.0962 (9)
H12A	0.3557	−0.0184	0.4977	0.115*
H12B	0.3372	−0.0740	0.3929	0.115*
O1	0.21428 (13)	0.37222 (15)	0.60152 (11)	0.0703 (4)
O2	0.23737 (13)	0.20801 (16)	0.48402 (11)	0.0697 (4)
P1	0.30007 (4)	0.34321 (6)	0.52851 (4)	0.05549 (14)
S1	0.46025 (5)	0.31190 (6)	0.58542 (4)	0.07012 (17)
S2	0.31804 (4)	0.50271 (6)	0.43864 (4)	0.06809 (16)
Ni1	0.5000	0.5000	0.5000	0.04798 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0597 (12)	0.0596 (11)	0.0783 (14)	−0.0170 (10)	0.0127 (11)	−0.0223 (10)
C2	0.102 (2)	0.0563 (13)	0.1013 (19)	0.0044 (13)	−0.0094 (16)	−0.0053 (13)
C3	0.0587 (15)	0.100 (2)	0.153 (3)	0.0155 (14)	−0.0041 (18)	−0.037 (2)
C4	0.104 (3)	0.117 (3)	0.172 (4)	−0.035 (2)	0.083 (3)	−0.071 (3)
C5	0.183 (4)	0.096 (2)	0.0595 (14)	−0.030 (2)	0.0373 (19)	−0.0063 (14)
C6	0.093 (2)	0.0959 (18)	0.0716 (15)	0.0153 (15)	−0.0166 (14)	−0.0242 (14)
C7	0.0696 (14)	0.0764 (14)	0.0626 (12)	−0.0009 (11)	0.0257 (11)	−0.0135 (10)
C8	0.124 (2)	0.0959 (19)	0.0572 (13)	0.0133 (17)	0.0104 (15)	0.0015 (12)
C9	0.090 (2)	0.158 (3)	0.090 (2)	−0.013 (2)	−0.0210 (17)	−0.022 (2)
C10	0.163 (4)	0.110 (3)	0.150 (3)	−0.060 (3)	0.032 (3)	−0.053 (3)
C11	0.180 (4)	0.0571 (15)	0.122 (3)	0.0009 (19)	0.043 (3)	0.0090 (16)
C12	0.105 (2)	0.095 (2)	0.0896 (18)	0.0414 (17)	0.0168 (16)	0.0003 (15)
O1	0.0693 (9)	0.0658 (9)	0.0817 (10)	−0.0261 (7)	0.0336 (8)	−0.0289 (7)
O2	0.0651 (9)	0.0742 (9)	0.0754 (9)	−0.0212 (7)	0.0311 (8)	−0.0259 (8)
P1	0.0473 (3)	0.0593 (3)	0.0620 (3)	−0.0131 (2)	0.0153 (2)	−0.0050 (2)
S1	0.0559 (3)	0.0720 (3)	0.0814 (4)	−0.0094 (2)	0.0037 (3)	0.0273 (3)
S2	0.0425 (3)	0.0825 (4)	0.0774 (3)	−0.0076 (2)	−0.0006 (2)	0.0215 (3)
Ni1	0.03693 (17)	0.05381 (19)	0.05351 (19)	−0.00500 (13)	0.00660 (13)	0.00798 (14)

Geometric parameters (Å, º)

C1—O1	1.469 (2)	C8—H8A	0.9700
C1—C2	1.477 (3)	C8—H8B	0.9700
C1—C6	1.486 (4)	C9—C10	1.497 (5)
C1—H1	0.9800	C9—H9A	0.9700
C2—C3	1.494 (4)	C9—H9B	0.9700
C2—H2A	0.9700	C10—C11	1.502 (5)
C2—H2B	0.9700	C10—H10A	0.9700
C3—C4	1.481 (5)	C10—H10B	0.9700
C3—H3A	0.9700	C11—C12	1.508 (5)
C3—H3B	0.9700	C11—H11A	0.9700
C4—C5	1.498 (5)	C11—H11B	0.9700
C4—H4A	0.9700	C12—H12A	0.9700
C4—H4B	0.9700	C12—H12B	0.9700
C5—C6	1.519 (4)	O1—P1	1.5566 (14)
C5—H5A	0.9700	O2—P1	1.5610 (14)
C5—H5B	0.9700	P1—S1	1.9879 (8)
C6—H6A	0.9700	P1—S2	1.9917 (8)
C6—H6B	0.9700	P1—Ni1	2.8470 (5)
C7—O2	1.462 (2)	S1—Ni1	2.2192 (5)
C7—C8	1.488 (4)	S2—Ni1	2.2202 (5)
C7—C12	1.497 (3)	Ni1—S1^i	2.2192 (5)
C7—H7	0.9800	Ni1—S2^i	2.2202 (5)
C8—C9	1.516 (4)	Ni1—P1^i	2.8470 (5)
O1—C1—C2	107.12 (19)	C10—C9—H9B	109.4
O1—C1—C6	106.96 (19)	C8—C9—H9B	109.4
C2—C1—C6	112.7 (2)	H9A—C9—H9B	108.0
O1—C1—H1	110.0	C9—C10—C11	110.6 (3)
C2—C1—H1	110.0	C9—C10—H10A	109.5
C6—C1—H1	110.0	C11—C10—H10A	109.5
C1—C2—C3	111.5 (2)	C9—C10—H10B	109.5
C1—C2—H2A	109.3	C11—C10—H10B	109.5
C3—C2—H2A	109.3	H10A—C10—H10B	108.1
C1—C2—H2B	109.3	C10—C11—C12	111.4 (3)
C3—C2—H2B	109.3	C10—C11—H11A	109.4
H2A—C2—H2B	108.0	C12—C11—H11A	109.4
C4—C3—C2	111.5 (3)	C10—C11—H11B	109.4
C4—C3—H3A	109.3	C12—C11—H11B	109.4
C2—C3—H3A	109.3	H11A—C11—H11B	108.0
C4—C3—H3B	109.3	C7—C12—C11	111.5 (2)
C2—C3—H3B	109.3	C7—C12—H12A	109.3
H3A—C3—H3B	108.0	C11—C12—H12A	109.3
C3—C4—C5	112.0 (2)	C7—C12—H12B	109.3
C3—C4—H4A	109.2	C11—C12—H12B	109.3
C5—C4—H4A	109.2	H12A—C12—H12B	108.0
C3—C4—H4B	109.2	C1—O1—P1	123.42 (12)
C5—C4—H4B	109.2	C7—O2—P1	122.28 (13)
H4A—C4—H4B	107.9	O1—P1—O2	95.56 (7)
C4—C5—C6	111.0 (3)	O1—P1—S1	114.59 (7)
C4—C5—H5A	109.4	O2—P1—S1	115.34 (7)
C6—C5—H5A	109.4	O1—P1—S2	115.07 (7)
C4—C5—H5B	109.4	O2—P1—S2	115.37 (7)
C6—C5—H5B	109.4	S1—P1—S2	101.74 (3)
H5A—C5—H5B	108.0	O1—P1—Ni1	128.31 (5)
C1—C6—C5	111.1 (2)	O2—P1—Ni1	136.13 (6)
C1—C6—H6A	109.4	S1—P1—Ni1	50.941 (18)
C5—C6—H6A	109.4	S2—P1—Ni1	50.961 (18)
C1—C6—H6B	109.4	P1—S1—Ni1	84.99 (2)
C5—C6—H6B	109.4	P1—S2—Ni1	84.87 (2)
H6A—C6—H6B	108.0	S1^i—Ni1—S1	180.000 (19)
O2—C7—C8	107.4 (2)	S1^i—Ni1—S2	91.89 (2)
O2—C7—C12	107.01 (19)	S1—Ni1—S2	88.11 (2)
C8—C7—C12	112.5 (2)	S1^i—Ni1—S2^i	88.11 (2)
O2—C7—H7	109.9	S1—Ni1—S2^i	91.89 (2)
C8—C7—H7	109.9	S2—Ni1—S2^i	180.0
C12—C7—H7	109.9	S1^i—Ni1—P1	135.927 (18)
C7—C8—C9	111.8 (2)	S1—Ni1—P1	44.073 (18)
C7—C8—H8A	109.3	S2—Ni1—P1	44.168 (18)
C9—C8—H8A	109.3	S2^i—Ni1—P1	135.832 (18)
C7—C8—H8B	109.3	S1^i—Ni1—P1^i	44.073 (18)
C9—C8—H8B	109.3	S1—Ni1—P1^i	135.927 (18)
H8A—C8—H8B	107.9	S2—Ni1—P1^i	135.832 (18)
C10—C9—C8	111.2 (3)	S2^i—Ni1—P1^i	44.168 (18)
C10—C9—H9A	109.4	P1—Ni1—P1^i	180.00 (2)
C8—C9—H9A	109.4
O1—C1—C2—C3	62.6 (3)	C7—O2—P1—Ni1	−1.2 (2)
C6—C1—C2—C3	−54.7 (3)	O1—P1—S1—Ni1	−120.43 (6)
C1—C2—C3—C4	54.9 (3)	O2—P1—S1—Ni1	130.01 (7)
C2—C3—C4—C5	−55.1 (3)	S2—P1—S1—Ni1	4.39 (3)
C3—C4—C5—C6	54.1 (3)	O1—P1—S2—Ni1	120.12 (7)
O1—C1—C6—C5	−63.7 (3)	O2—P1—S2—Ni1	−129.99 (7)
C2—C1—C6—C5	53.7 (3)	S1—P1—S2—Ni1	−4.38 (3)
C4—C5—C6—C1	−52.9 (3)	P1—S1—Ni1—S2	−3.85 (3)
O2—C7—C8—C9	−64.9 (3)	P1—S1—Ni1—S2^i	176.15 (3)
C12—C7—C8—C9	52.6 (3)	P1—S1—Ni1—P1^i	180.0
C7—C8—C9—C10	−54.4 (4)	P1—S2—Ni1—S1^i	−176.15 (3)
C8—C9—C10—C11	56.2 (4)	P1—S2—Ni1—S1	3.85 (3)
C9—C10—C11—C12	−56.7 (4)	P1—S2—Ni1—P1^i	180.0
O2—C7—C12—C11	64.9 (3)	O1—P1—Ni1—S1^i	−87.60 (10)
C8—C7—C12—C11	−52.8 (3)	O2—P1—Ni1—S1^i	92.80 (11)
C10—C11—C12—C7	54.7 (4)	S1—P1—Ni1—S1^i	180.0
C2—C1—O1—P1	113.6 (2)	S2—P1—Ni1—S1^i	5.53 (4)
C6—C1—O1—P1	−125.34 (19)	O1—P1—Ni1—S1	92.40 (10)
C8—C7—O2—P1	−118.7 (2)	O2—P1—Ni1—S1	−87.20 (11)
C12—C7—O2—P1	120.2 (2)	S2—P1—Ni1—S1	−174.47 (4)
C1—O1—P1—O2	−172.73 (18)	O1—P1—Ni1—S2	−93.13 (10)
C1—O1—P1—S1	66.10 (18)	O2—P1—Ni1—S2	87.27 (11)
C1—O1—P1—S2	−51.35 (19)	S1—P1—Ni1—S2	174.47 (4)
C1—O1—P1—Ni1	7.5 (2)	O1—P1—Ni1—S2^i	86.87 (10)
C7—O2—P1—O1	179.15 (17)	O2—P1—Ni1—S2^i	−92.73 (11)
C7—O2—P1—S1	−60.27 (18)	S1—P1—Ni1—S2^i	−5.53 (4)
C7—O2—P1—S2	57.99 (19)	S2—P1—Ni1—S2^i	180.0

Symmetry code: (i) −x+1, −y+1, −z+1.