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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 NiII atom lies on a crystallographic center of symmetry in a distorted square-planar coodination environment.
Supporting information
CCDC reference: 283947
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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)
top
Crystal data top
[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) Å3 | 0.58 × 0.48 × 0.07 mm |
Z = 2 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0384P)2 + 0.2064P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—S1i | 2.2192 (5) |
C7—H7 | 0.9800 | Ni1—S2i | 2.2202 (5) |
C8—C9 | 1.516 (4) | Ni1—P1i | 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 | S1i—Ni1—S1 | 180.000 (19) |
O2—C7—C8 | 107.4 (2) | S1i—Ni1—S2 | 91.89 (2) |
O2—C7—C12 | 107.01 (19) | S1—Ni1—S2 | 88.11 (2) |
C8—C7—C12 | 112.5 (2) | S1i—Ni1—S2i | 88.11 (2) |
O2—C7—H7 | 109.9 | S1—Ni1—S2i | 91.89 (2) |
C8—C7—H7 | 109.9 | S2—Ni1—S2i | 180.0 |
C12—C7—H7 | 109.9 | S1i—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 | S2i—Ni1—P1 | 135.832 (18) |
C7—C8—H8B | 109.3 | S1i—Ni1—P1i | 44.073 (18) |
C9—C8—H8B | 109.3 | S1—Ni1—P1i | 135.927 (18) |
H8A—C8—H8B | 107.9 | S2—Ni1—P1i | 135.832 (18) |
C10—C9—C8 | 111.2 (3) | S2i—Ni1—P1i | 44.168 (18) |
C10—C9—H9A | 109.4 | P1—Ni1—P1i | 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—S2i | 176.15 (3) |
C12—C7—C8—C9 | 52.6 (3) | P1—S1—Ni1—P1i | 180.0 |
C7—C8—C9—C10 | −54.4 (4) | P1—S2—Ni1—S1i | −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—P1i | 180.0 |
O2—C7—C12—C11 | 64.9 (3) | O1—P1—Ni1—S1i | −87.60 (10) |
C8—C7—C12—C11 | −52.8 (3) | O2—P1—Ni1—S1i | 92.80 (11) |
C10—C11—C12—C7 | 54.7 (4) | S1—P1—Ni1—S1i | 180.0 |
C2—C1—O1—P1 | 113.6 (2) | S2—P1—Ni1—S1i | 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—S2i | 86.87 (10) |
C7—O2—P1—O1 | 179.15 (17) | O2—P1—Ni1—S2i | −92.73 (11) |
C7—O2—P1—S1 | −60.27 (18) | S1—P1—Ni1—S2i | −5.53 (4) |
C7—O2—P1—S2 | 57.99 (19) | S2—P1—Ni1—S2i | 180.0 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Selected geometric parameters for complexes (I)–(IV) topDistances (Å) | (I) | (II) | (III) | (IV) | (V)b |
Ni—S1 | 2,2192 (5) | 2.221 (3) | 2,2330 (6) | 2,2298 (6) | 2,411 (2) |
Ni—S2 | 2,2202 (5) | 2.217 (3) | 2,2413 (6) | 2,2327 (6) | 2,369 (2) |
P1—S1 | 1,9879 (8) | 1.982 (4) | 2,0043 (8) | 2,0042 (8) | 1,955 (3) |
P1—S2 | 1,9917 (8) | 1.992 (4) | 2,0048 (7) | 2,0082 (8) | 1,992 (3) |
P1—O1 | 1,5566 (14) | 1.565 (6) | 1.7904 (18)a | 1.792 (2)a | 1,569 (5) |
P1—O2 | 1,5610 (14) | 1.568 (7) | 1.5856 (13) | 1.5855 (15) | 1,572 (6) |
| | | | | |
Angles (°) | | | | | |
S1—Ni—S2 | 88,11 (2) | 88.01 (10) | 88,87 (2) | 88,50 (2) | 85,62 (8) |
S1—P1—S2 | 101,74 (3) | 101.75 (16) | 102,77 (3) | 101,80 (3) | 109,12 (13) |
P1—S1—Ni | 84,99 (2) | 85.02 (13) | 82,38 (2) | 83,43 (2) | 81,99 (10) |
P1—S2—Ni | 84,87 (2) | 84.91 (13) | 82,58 (3) | 83,26 (2) | 83,14 (9) |
O1—P1—S2 | 115,07 (7) | 114.0 (3) | 112.57 (7)a | 114.18 (8)a | 113,4(2) |
O2—P1—S1 | 115,34 (7) | 115.4 (3) | 113.59 (6) | 114.90 (6) | 113,4(2) |
O1—P1—O2 | 95.56 (7) | 95.9 (3) | 101.82 (7)a | 100.02 (9)a | 96.4 (3) |
Notes: (a) In (III) and (IV), atom O1 is replaced by C1; (b) the terminal
bonding of the ligands in the dimeric Zn complex were used for comparison. |
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