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metal-organic compounds
The title compound, [Ni(C14H14O2PS2)2], consists of discrete molecules with the Ni atom chelated by both S atoms of the p-tolyldithiophosphate ligands in a bidentate manner in a four-coordinate environment. The molecule has inversion symmetry about the Ni atom, and the geometry is nearly perfect square planar, with S—Ni—S chelate bond angles of 89.12 (2)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006440/om6221sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006440/om6221Isup2.hkl |
CCDC reference: 238677
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.083
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - S1 .. 6.29 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - S2 .. 6.58 su PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 3 S1 -NI1 -S1 -P1 -15.00100.00 2.765 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 5 S2 -NI1 -S2 -P1 165.00100.00 2.765 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 19 P1 -NI1 -P1 -O1 76.00100.00 2.765 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 24 P1 -NI1 -P1 -O2 -101.00100.00 2.765 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 28 P1 -NI1 -P1 -S2 -14.00100.00 2.765 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 32 P1 -NI1 -P1 -S1 172.00100.00 2.765 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 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 2 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 7 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Crystal data top
[Ni(C14H14O2PS2)2] | Z = 1 |
Mr = 677.39 | F(000) = 350 |
Triclinic, P1 | Dx = 1.446 Mg m−3 |
a = 7.1884 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.3158 (14) Å | Cell parameters from 4396 reflections |
c = 12.1699 (18) Å | θ = 1.7–26.0° |
α = 78.605 (2)° | µ = 1.03 mm−1 |
β = 81.335 (2)° | T = 293 K |
γ = 78.557 (2)° | Block, purple |
V = 777.7 (2) Å3 | 0.48 × 0.26 × 0.23 mm |
Data collection top
Bruker SMART APEX diffractometer | 3031 independent reflections |
Radiation source: fine-focus sealed tube | 2789 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 83.7 pixels mm-1 | θmax = 26.0°, θmin = 1.7° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −11→11 |
Tmin = 0.638, Tmax = 0.798 | l = −14→14 |
8064 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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0471P)2 + 0.1517P] where P = (Fo2 + 2Fc2)/3 |
3031 reflections | (Δ/σ)max < 0.001 |
180 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ni1 | 1.0000 | 0.5000 | 0.0000 | 0.04015 (11) | |
S1 | 0.83981 (7) | 0.32810 (6) | 0.10454 (4) | 0.05265 (15) | |
S2 | 1.15284 (7) | 0.49485 (6) | 0.14752 (4) | 0.05311 (15) | |
P1 | 0.98029 (7) | 0.35593 (5) | 0.22444 (4) | 0.04372 (13) | |
O1 | 0.84886 (19) | 0.42237 (15) | 0.32546 (11) | 0.0522 (3) | |
O2 | 1.08360 (19) | 0.20555 (15) | 0.29290 (11) | 0.0532 (3) | |
C1 | 0.5089 (3) | 0.4516 (2) | 0.36319 (17) | 0.0539 (5) | |
H1 | 0.4991 | 0.5393 | 0.3107 | 0.065* | |
C2 | 0.3474 (3) | 0.4047 (3) | 0.42487 (18) | 0.0585 (5) | |
H2 | 0.2281 | 0.4621 | 0.4135 | 0.070* | |
C3 | 0.3590 (3) | 0.2750 (3) | 0.50272 (18) | 0.0601 (5) | |
C4 | 0.5379 (3) | 0.1908 (3) | 0.51718 (19) | 0.0626 (5) | |
H4 | 0.5485 | 0.1021 | 0.5686 | 0.075* | |
C5 | 0.7009 (3) | 0.2357 (2) | 0.45680 (18) | 0.0570 (5) | |
H5 | 0.8204 | 0.1782 | 0.4674 | 0.068* | |
C6 | 0.6844 (3) | 0.3657 (2) | 0.38120 (15) | 0.0461 (4) | |
C7 | 0.1825 (4) | 0.2272 (4) | 0.5721 (2) | 0.0869 (8) | |
H7A | 0.1765 | 0.2455 | 0.6476 | 0.130* | |
H7B | 0.1875 | 0.1230 | 0.5740 | 0.130* | |
H7C | 0.0711 | 0.2827 | 0.5390 | 0.130* | |
C8 | 1.1682 (3) | −0.0173 (2) | 0.2140 (2) | 0.0675 (6) | |
H8 | 1.0408 | −0.0291 | 0.2275 | 0.081* | |
C9 | 1.3066 (4) | −0.1217 (3) | 0.1671 (2) | 0.0792 (7) | |
H9 | 1.2709 | −0.2044 | 0.1497 | 0.095* | |
C10 | 1.4946 (4) | −0.1055 (3) | 0.14589 (19) | 0.0684 (6) | |
C11 | 1.5431 (3) | 0.0168 (3) | 0.1741 (2) | 0.0656 (6) | |
H11 | 1.6703 | 0.0291 | 0.1610 | 0.079* | |
C12 | 1.4087 (3) | 0.1219 (2) | 0.22133 (18) | 0.0559 (5) | |
H12 | 1.4441 | 0.2039 | 0.2401 | 0.067* | |
C13 | 1.2225 (3) | 0.1026 (2) | 0.23983 (15) | 0.0473 (4) | |
C14 | 1.6438 (5) | −0.2202 (3) | 0.0944 (3) | 0.1055 (11) | |
H14A | 1.7214 | −0.2775 | 0.1509 | 0.158* | |
H14B | 1.7230 | −0.1709 | 0.0338 | 0.158* | |
H14C | 1.5817 | −0.2849 | 0.0657 | 0.158* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.04168 (19) | 0.03780 (18) | 0.04014 (19) | −0.01007 (13) | −0.00313 (13) | −0.00280 (13) |
S1 | 0.0608 (3) | 0.0539 (3) | 0.0472 (3) | −0.0265 (2) | −0.0067 (2) | −0.0009 (2) |
S2 | 0.0568 (3) | 0.0574 (3) | 0.0483 (3) | −0.0241 (2) | −0.0107 (2) | 0.0012 (2) |
P1 | 0.0470 (3) | 0.0418 (3) | 0.0402 (3) | −0.0092 (2) | −0.00134 (19) | −0.00343 (19) |
O1 | 0.0543 (8) | 0.0490 (7) | 0.0526 (8) | −0.0098 (6) | 0.0034 (6) | −0.0134 (6) |
O2 | 0.0558 (8) | 0.0500 (8) | 0.0439 (7) | −0.0002 (6) | 0.0025 (6) | 0.0002 (6) |
C1 | 0.0593 (12) | 0.0558 (11) | 0.0439 (10) | 0.0007 (9) | −0.0091 (9) | −0.0106 (9) |
C2 | 0.0470 (11) | 0.0765 (15) | 0.0526 (12) | 0.0006 (10) | −0.0085 (9) | −0.0220 (11) |
C3 | 0.0536 (12) | 0.0827 (15) | 0.0493 (11) | −0.0183 (11) | −0.0009 (9) | −0.0211 (11) |
C4 | 0.0642 (13) | 0.0628 (13) | 0.0560 (12) | −0.0140 (11) | −0.0032 (10) | 0.0010 (10) |
C5 | 0.0483 (11) | 0.0588 (12) | 0.0577 (12) | −0.0015 (9) | −0.0053 (9) | −0.0036 (10) |
C6 | 0.0464 (10) | 0.0500 (10) | 0.0417 (9) | −0.0072 (8) | 0.0003 (7) | −0.0128 (8) |
C7 | 0.0644 (15) | 0.124 (2) | 0.0768 (17) | −0.0361 (15) | 0.0072 (13) | −0.0195 (16) |
C8 | 0.0625 (13) | 0.0506 (12) | 0.0885 (17) | −0.0173 (10) | −0.0052 (12) | −0.0051 (11) |
C9 | 0.101 (2) | 0.0435 (12) | 0.0956 (19) | −0.0126 (12) | −0.0139 (16) | −0.0155 (12) |
C10 | 0.0821 (16) | 0.0512 (12) | 0.0552 (12) | 0.0107 (11) | 0.0024 (11) | 0.0001 (10) |
C11 | 0.0544 (12) | 0.0612 (13) | 0.0687 (14) | −0.0010 (10) | 0.0039 (10) | 0.0011 (11) |
C12 | 0.0552 (12) | 0.0500 (11) | 0.0609 (12) | −0.0088 (9) | −0.0061 (9) | −0.0068 (9) |
C13 | 0.0522 (10) | 0.0404 (9) | 0.0426 (10) | −0.0033 (8) | 0.0002 (8) | −0.0001 (7) |
C14 | 0.134 (3) | 0.0707 (17) | 0.083 (2) | 0.0332 (18) | 0.0112 (18) | −0.0134 (15) |
Geometric parameters (Å, º) top
Ni1—S2i | 2.2298 (5) | C4—H4 | 0.9300 |
Ni1—S2 | 2.2298 (5) | C5—C6 | 1.365 (3) |
Ni1—S1 | 2.2348 (5) | C5—H5 | 0.9300 |
Ni1—S1i | 2.2348 (5) | C7—H7A | 0.9600 |
Ni1—P1 | 2.7914 (6) | C7—H7B | 0.9600 |
Ni1—P1i | 2.7914 (6) | C7—H7C | 0.9600 |
S1—P1 | 1.9782 (7) | C8—C13 | 1.359 (3) |
S2—P1 | 1.9743 (7) | C8—C9 | 1.388 (3) |
P1—O1 | 1.5830 (13) | C8—H8 | 0.9300 |
P1—O2 | 1.5877 (14) | C9—C10 | 1.370 (4) |
O1—C6 | 1.414 (2) | C9—H9 | 0.9300 |
O2—C13 | 1.416 (2) | C10—C11 | 1.374 (3) |
C1—C6 | 1.376 (3) | C10—C14 | 1.514 (3) |
C1—C2 | 1.382 (3) | C11—C12 | 1.379 (3) |
C1—H1 | 0.9300 | C11—H11 | 0.9300 |
C2—C3 | 1.377 (3) | C12—C13 | 1.365 (3) |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
C3—C4 | 1.384 (3) | C14—H14A | 0.9600 |
C3—C7 | 1.508 (3) | C14—H14B | 0.9600 |
C4—C5 | 1.379 (3) | C14—H14C | 0.9600 |
S2i—Ni1—S2 | 180.00 (3) | C5—C4—H4 | 119.4 |
S2i—Ni1—S1 | 90.88 (2) | C3—C4—H4 | 119.4 |
S2—Ni1—S1 | 89.12 (2) | C6—C5—C4 | 119.06 (19) |
S2i—Ni1—S1i | 89.12 (2) | C6—C5—H5 | 120.5 |
S2—Ni1—S1i | 90.88 (2) | C4—C5—H5 | 120.5 |
S1—Ni1—S1i | 180.000 (19) | C5—C6—C1 | 121.42 (18) |
S2i—Ni1—P1 | 135.416 (17) | C5—C6—O1 | 120.67 (17) |
S2—Ni1—P1 | 44.584 (17) | C1—C6—O1 | 117.73 (17) |
S1—Ni1—P1 | 44.670 (16) | C3—C7—H7A | 109.5 |
S1i—Ni1—P1 | 135.330 (16) | C3—C7—H7B | 109.5 |
S2i—Ni1—P1i | 44.584 (17) | H7A—C7—H7B | 109.5 |
S2—Ni1—P1i | 135.416 (17) | C3—C7—H7C | 109.5 |
S1—Ni1—P1i | 135.330 (16) | H7A—C7—H7C | 109.5 |
S1i—Ni1—P1i | 44.670 (16) | H7B—C7—H7C | 109.5 |
P1—Ni1—P1i | 180.0 | C13—C8—C9 | 118.7 (2) |
P1—S1—Ni1 | 82.75 (2) | C13—C8—H8 | 120.7 |
P1—S2—Ni1 | 82.97 (2) | C9—C8—H8 | 120.7 |
O1—P1—O2 | 99.39 (7) | C10—C9—C8 | 121.5 (2) |
O1—P1—S2 | 109.61 (6) | C10—C9—H9 | 119.3 |
O2—P1—S2 | 114.56 (6) | C8—C9—H9 | 119.3 |
O1—P1—S1 | 114.46 (6) | C9—C10—C11 | 117.8 (2) |
O2—P1—S1 | 114.23 (6) | C9—C10—C14 | 120.8 (3) |
S2—P1—S1 | 104.85 (3) | C11—C10—C14 | 121.3 (3) |
O1—P1—Ni1 | 124.27 (6) | C10—C11—C12 | 121.9 (2) |
O2—P1—Ni1 | 136.28 (5) | C10—C11—H11 | 119.0 |
S2—P1—Ni1 | 52.448 (18) | C12—C11—H11 | 119.0 |
S1—P1—Ni1 | 52.578 (19) | C13—C12—C11 | 118.4 (2) |
C6—O1—P1 | 122.93 (12) | C13—C12—H12 | 120.8 |
C13—O2—P1 | 122.33 (11) | C11—C12—H12 | 120.8 |
C6—C1—C2 | 118.5 (2) | C8—C13—C12 | 121.70 (19) |
C6—C1—H1 | 120.7 | C8—C13—O2 | 118.89 (18) |
C2—C1—H1 | 120.7 | C12—C13—O2 | 119.32 (18) |
C3—C2—C1 | 121.6 (2) | C10—C14—H14A | 109.5 |
C3—C2—H2 | 119.2 | C10—C14—H14B | 109.5 |
C1—C2—H2 | 119.2 | H14A—C14—H14B | 109.5 |
C2—C3—C4 | 118.1 (2) | C10—C14—H14C | 109.5 |
C2—C3—C7 | 121.1 (2) | H14A—C14—H14C | 109.5 |
C4—C3—C7 | 120.7 (2) | H14B—C14—H14C | 109.5 |
C5—C4—C3 | 121.3 (2) | ||
S2i—Ni1—S1—P1 | −176.06 (2) | O2—P1—O1—C6 | −73.46 (15) |
S2—Ni1—S1—P1 | 3.94 (2) | S2—P1—O1—C6 | 166.14 (13) |
S1i—Ni1—S1—P1 | −15 (100) | S1—P1—O1—C6 | 48.69 (15) |
P1i—Ni1—S1—P1 | 180.0 | Ni1—P1—O1—C6 | 108.83 (13) |
S2i—Ni1—S2—P1 | 165 (100) | O1—P1—O2—C13 | −179.14 (14) |
S1—Ni1—S2—P1 | −3.95 (2) | S2—P1—O2—C13 | −62.43 (15) |
S1i—Ni1—S2—P1 | 176.05 (2) | S1—P1—O2—C13 | 58.54 (15) |
P1i—Ni1—S2—P1 | 180.0 | Ni1—P1—O2—C13 | −1.88 (19) |
Ni1—S2—P1—O1 | −118.70 (6) | C6—C1—C2—C3 | −0.2 (3) |
Ni1—S2—P1—O2 | 130.62 (6) | C1—C2—C3—C4 | −0.7 (3) |
Ni1—S2—P1—S1 | 4.62 (3) | C1—C2—C3—C7 | 178.1 (2) |
Ni1—S1—P1—O1 | 115.53 (6) | C2—C3—C4—C5 | 0.9 (3) |
Ni1—S1—P1—O2 | −130.82 (6) | C7—C3—C4—C5 | −177.9 (2) |
Ni1—S1—P1—S2 | −4.61 (3) | C3—C4—C5—C6 | −0.2 (3) |
S2i—Ni1—P1—O1 | −90.66 (7) | C4—C5—C6—C1 | −0.8 (3) |
S2—Ni1—P1—O1 | 89.34 (7) | C4—C5—C6—O1 | 174.12 (18) |
S1—Ni1—P1—O1 | −96.29 (7) | C2—C1—C6—C5 | 1.0 (3) |
S1i—Ni1—P1—O1 | 83.71 (7) | C2—C1—C6—O1 | −174.06 (16) |
P1i—Ni1—P1—O1 | 76 (100) | P1—O1—C6—C5 | 75.9 (2) |
S2i—Ni1—P1—O2 | 92.61 (9) | P1—O1—C6—C1 | −109.00 (18) |
S2—Ni1—P1—O2 | −87.39 (9) | C13—C8—C9—C10 | −0.5 (4) |
S1—Ni1—P1—O2 | 86.98 (9) | C8—C9—C10—C11 | 0.9 (4) |
S1i—Ni1—P1—O2 | −93.02 (9) | C8—C9—C10—C14 | −179.8 (2) |
P1i—Ni1—P1—O2 | −101 (100) | C9—C10—C11—C12 | −0.6 (4) |
S2i—Ni1—P1—S2 | 180.0 | C14—C10—C11—C12 | −179.8 (2) |
S1—Ni1—P1—S2 | 174.38 (3) | C10—C11—C12—C13 | −0.2 (3) |
S1i—Ni1—P1—S2 | −5.62 (3) | C9—C8—C13—C12 | −0.4 (3) |
P1i—Ni1—P1—S2 | −14 (100) | C9—C8—C13—O2 | −176.9 (2) |
S2i—Ni1—P1—S1 | 5.62 (3) | C11—C12—C13—C8 | 0.7 (3) |
S2—Ni1—P1—S1 | −174.38 (3) | C11—C12—C13—O2 | 177.16 (18) |
S1i—Ni1—P1—S1 | 180.0 | P1—O2—C13—C8 | −97.9 (2) |
P1i—Ni1—P1—S1 | 172 (100) | P1—O2—C13—C12 | 85.6 (2) |
Symmetry code: (i) −x+2, −y+1, −z. |
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