metal-organic compounds
(meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane)nickel(II) bis(O,O′-dibenzyl dithiophosphate)
aDepartment of Chemistry, Sichuan University of Science & Engineering, Zigong, Sichuan 643000, People's Republic of China
*Correspondence e-mail: zoulike@yahoo.com.cn
In the title salt-type 1:2 adduct, [Ni(C16H36N4)](C14H14O2PS2)2 or [Ni(tet-a)][S2P(OCH2Ph)2]2, where tet-a is meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, the [Ni(tet-a)]2+ complex cation exhibits a relatively undistorted square-planar geometry about the Ni atom, which lies on an inversion centre and is coordinated by four macrocyclic N atoms. The two O,O′-bis(2-phenylmethyl) dithiophosphate anions act as counter-ions to balance the charge and they interact with the complex through N—H⋯S hydrogen bonds. Important geometric data include Ni—N distances of 1.958 (3) and 1.963 (3) Å.
Related literature
For related literature, see: Burchell et al. (2000); Ali et al. (2004); Allen (2002); Li et al. (2006); Liu et al. (1997).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536808008398/dn2324sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008398/dn2324Isup2.hkl
A hot solution of tet-a.2H2O (0.77 g, 2 mmol) and Ni(OAc)2.2H2O (0.25 g, 1 mmol) in 20 ml me thanol was quickly added to a hot solution of (PhCH2O)2PSSNH2(C2H5)2(0.77 g, 2 mmol) in 20 ml me thanol. The mixture was refluxed for 6 h, then cooled to room temperature, the orange-red precipitate was collected by filtration, washed with small amounts of methanol.A solution of adduct (1) in DMSO was kept at room temperature, and red block crystals suitable for X-ray diffraction studies were obtained in eight months,.
All H atoms attached to C and N atom were fixed geometrically and treated as riding with C—H = 0.98 Å (methine), 0.97 Å (methylene), 0.96Å (methyl) or 0.93Å (aromatic) and N—H = 0.91 Å with Uiso(H) = 1.2Ueq(C, N) or Uiso(H) = 1.5Ueq(methyl).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).[Ni(C16H36N4)](C14H14O2PS2)2 | F(000) = 1020 |
Mr = 961.88 | Dx = 1.348 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 19 reflections |
a = 16.371 (5) Å | θ = 4.4–5.5° |
b = 14.917 (5) Å | µ = 0.70 mm−1 |
c = 9.964 (4) Å | T = 290 K |
β = 103.11 (3)° | Block, red |
V = 2369.9 (15) Å3 | 0.40 × 0.38 × 0.36 mm |
Z = 2 |
Enraf–Nonius CAD-4 diffractometer | 2880 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 25.5°, θmin = 1.3° |
ω/2θ scans | h = −7→19 |
Absorption correction: ψ scan (North et al., 1968) | k = −18→0 |
Tmin = 0.768, Tmax = 0.787 | l = −12→11 |
5571 measured reflections | 3 standard reflections every 300 reflections |
4393 independent reflections | intensity decay: 1.1% |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0689P)2] where P = (Fo2 + 2Fc2)/3 |
4393 reflections | (Δ/σ)max < 0.001 |
275 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
[Ni(C16H36N4)](C14H14O2PS2)2 | V = 2369.9 (15) Å3 |
Mr = 961.88 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.371 (5) Å | µ = 0.70 mm−1 |
b = 14.917 (5) Å | T = 290 K |
c = 9.964 (4) Å | 0.40 × 0.38 × 0.36 mm |
β = 103.11 (3)° |
Enraf–Nonius CAD-4 diffractometer | 2880 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.021 |
Tmin = 0.768, Tmax = 0.787 | 3 standard reflections every 300 reflections |
5571 measured reflections | intensity decay: 1.1% |
4393 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.52 e Å−3 |
4393 reflections | Δρmin = −0.34 e Å−3 |
275 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.5000 | 0.5000 | 0.0000 | 0.02975 (18) | |
S1 | 0.39590 (6) | 0.45749 (7) | 0.26928 (12) | 0.0569 (3) | |
S2 | 0.28652 (6) | 0.64383 (7) | 0.13356 (11) | 0.0498 (3) | |
P1 | 0.29136 (6) | 0.52753 (7) | 0.22790 (10) | 0.0406 (3) | |
O1 | 0.26427 (15) | 0.53665 (18) | 0.3726 (3) | 0.0509 (7) | |
O2 | 0.21601 (15) | 0.47114 (17) | 0.1325 (3) | 0.0521 (7) | |
N1 | 0.57052 (16) | 0.53521 (17) | 0.1790 (3) | 0.0341 (7) | |
H1 | 0.5357 | 0.5294 | 0.2379 | 0.041* | |
N2 | 0.55476 (16) | 0.38269 (17) | 0.0308 (3) | 0.0332 (6) | |
H2 | 0.5975 | 0.3845 | −0.0138 | 0.040* | |
C1 | 0.6346 (2) | 0.4648 (2) | 0.2251 (4) | 0.0543 (12) | |
H1A | 0.6539 | 0.4663 | 0.3245 | 0.065* | |
H1B | 0.6824 | 0.4747 | 0.1844 | 0.065* | |
C2 | 0.5955 (2) | 0.3765 (2) | 0.1806 (4) | 0.0478 (10) | |
H2A | 0.5540 | 0.3619 | 0.2330 | 0.057* | |
H2B | 0.6378 | 0.3298 | 0.1960 | 0.057* | |
C3 | 0.5074 (2) | 0.2981 (2) | −0.0165 (3) | 0.0353 (8) | |
H3 | 0.4636 | 0.2913 | 0.0354 | 0.042* | |
C4 | 0.4652 (2) | 0.3050 (2) | −0.1675 (4) | 0.0397 (9) | |
H4A | 0.4439 | 0.2462 | −0.1989 | 0.048* | |
H4B | 0.5077 | 0.3204 | −0.2174 | 0.048* | |
C5 | 0.5636 (2) | 0.2146 (2) | 0.0096 (4) | 0.0452 (9) | |
H5A | 0.6067 | 0.2194 | −0.0413 | 0.068* | |
H5B | 0.5304 | 0.1621 | −0.0197 | 0.068* | |
H5C | 0.5889 | 0.2101 | 0.1062 | 0.068* | |
C6 | 0.6063 (2) | 0.6282 (2) | 0.2081 (4) | 0.0359 (8) | |
C7 | 0.6734 (2) | 0.6441 (3) | 0.1263 (4) | 0.0542 (11) | |
H7A | 0.6523 | 0.6262 | 0.0323 | 0.081* | |
H7B | 0.7225 | 0.6096 | 0.1658 | 0.081* | |
H7C | 0.6877 | 0.7066 | 0.1293 | 0.081* | |
C8 | 0.6443 (2) | 0.6385 (3) | 0.3636 (4) | 0.0543 (11) | |
H8A | 0.6602 | 0.6998 | 0.3838 | 0.081* | |
H8B | 0.6928 | 0.6008 | 0.3896 | 0.081* | |
H8C | 0.6035 | 0.6212 | 0.4144 | 0.081* | |
C9 | 0.1889 (3) | 0.5872 (3) | 0.3782 (4) | 0.0624 (12) | |
H9A | 0.1446 | 0.5736 | 0.2982 | 0.075* | |
H9B | 0.2003 | 0.6510 | 0.3783 | 0.075* | |
C10 | 0.1620 (2) | 0.5621 (3) | 0.5064 (4) | 0.0511 (10) | |
C11 | 0.1766 (3) | 0.6179 (3) | 0.6203 (5) | 0.0639 (12) | |
H11 | 0.2020 | 0.6734 | 0.6175 | 0.077* | |
C12 | 0.1527 (3) | 0.5897 (5) | 0.7399 (5) | 0.0884 (18) | |
H12 | 0.1623 | 0.6266 | 0.8171 | 0.106* | |
C13 | 0.1153 (4) | 0.5082 (6) | 0.7433 (7) | 0.103 (2) | |
H13 | 0.0995 | 0.4899 | 0.8230 | 0.123* | |
C14 | 0.1010 (4) | 0.4537 (5) | 0.6318 (8) | 0.108 (2) | |
H14 | 0.0759 | 0.3980 | 0.6349 | 0.130* | |
C15 | 0.1237 (3) | 0.4810 (4) | 0.5149 (6) | 0.0822 (15) | |
H15 | 0.1130 | 0.4435 | 0.4383 | 0.099* | |
C16 | 0.2008 (2) | 0.3800 (3) | 0.1649 (5) | 0.0604 (12) | |
H16A | 0.1953 | 0.3756 | 0.2596 | 0.072* | |
H16B | 0.2473 | 0.3425 | 0.1542 | 0.072* | |
C17 | 0.1214 (2) | 0.3495 (2) | 0.0688 (4) | 0.0472 (10) | |
C18 | 0.0461 (3) | 0.3895 (3) | 0.0682 (5) | 0.0681 (13) | |
H18 | 0.0439 | 0.4365 | 0.1287 | 0.082* | |
C19 | −0.0272 (3) | 0.3613 (4) | −0.0213 (5) | 0.0795 (16) | |
H19 | −0.0781 | 0.3884 | −0.0193 | 0.095* | |
C20 | −0.0245 (3) | 0.2952 (4) | −0.1100 (6) | 0.0853 (18) | |
H20 | −0.0738 | 0.2751 | −0.1682 | 0.102* | |
C21 | 0.0503 (4) | 0.2567 (4) | −0.1159 (6) | 0.108 (2) | |
H21 | 0.0522 | 0.2126 | −0.1811 | 0.130* | |
C22 | 0.1229 (3) | 0.2831 (3) | −0.0256 (6) | 0.0808 (16) | |
H22 | 0.1734 | 0.2557 | −0.0286 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0297 (3) | 0.0263 (3) | 0.0308 (3) | 0.0014 (2) | 0.0017 (2) | 0.0013 (3) |
S1 | 0.0404 (5) | 0.0557 (6) | 0.0758 (8) | 0.0085 (5) | 0.0157 (5) | 0.0121 (6) |
S2 | 0.0506 (6) | 0.0459 (6) | 0.0535 (6) | −0.0007 (4) | 0.0129 (5) | 0.0074 (5) |
P1 | 0.0349 (5) | 0.0421 (5) | 0.0440 (6) | −0.0003 (4) | 0.0070 (4) | 0.0019 (4) |
O1 | 0.0459 (14) | 0.0648 (17) | 0.0443 (16) | 0.0157 (13) | 0.0152 (12) | 0.0131 (13) |
O2 | 0.0455 (14) | 0.0413 (14) | 0.0633 (18) | −0.0079 (11) | −0.0011 (13) | 0.0018 (13) |
N1 | 0.0367 (14) | 0.0292 (14) | 0.0336 (16) | 0.0000 (12) | 0.0023 (12) | 0.0011 (12) |
N2 | 0.0332 (14) | 0.0297 (15) | 0.0358 (16) | 0.0036 (11) | 0.0059 (12) | 0.0022 (12) |
C1 | 0.052 (2) | 0.037 (2) | 0.059 (3) | 0.0101 (17) | −0.019 (2) | −0.0037 (19) |
C2 | 0.058 (2) | 0.035 (2) | 0.039 (2) | 0.0084 (17) | −0.0113 (18) | 0.0016 (17) |
C3 | 0.0396 (18) | 0.0274 (16) | 0.038 (2) | −0.0049 (14) | 0.0082 (15) | −0.0018 (15) |
C4 | 0.0458 (19) | 0.0307 (18) | 0.041 (2) | −0.0024 (15) | 0.0071 (16) | −0.0022 (16) |
C5 | 0.060 (2) | 0.0301 (19) | 0.044 (2) | 0.0053 (16) | 0.0098 (18) | 0.0000 (17) |
C6 | 0.0390 (18) | 0.0301 (18) | 0.037 (2) | −0.0041 (14) | 0.0046 (15) | −0.0051 (15) |
C7 | 0.041 (2) | 0.056 (2) | 0.065 (3) | −0.0041 (18) | 0.0109 (19) | 0.006 (2) |
C8 | 0.058 (2) | 0.050 (2) | 0.045 (2) | 0.0027 (19) | −0.0075 (19) | −0.0090 (19) |
C9 | 0.060 (2) | 0.075 (3) | 0.056 (3) | 0.025 (2) | 0.020 (2) | 0.014 (2) |
C10 | 0.044 (2) | 0.061 (3) | 0.050 (3) | 0.019 (2) | 0.0147 (18) | 0.011 (2) |
C11 | 0.058 (3) | 0.073 (3) | 0.060 (3) | 0.019 (2) | 0.012 (2) | −0.001 (2) |
C12 | 0.083 (4) | 0.128 (5) | 0.055 (3) | 0.050 (4) | 0.018 (3) | −0.003 (3) |
C13 | 0.097 (4) | 0.138 (6) | 0.091 (5) | 0.063 (4) | 0.061 (4) | 0.053 (5) |
C14 | 0.114 (5) | 0.089 (5) | 0.146 (6) | 0.021 (4) | 0.080 (5) | 0.043 (5) |
C15 | 0.095 (4) | 0.077 (4) | 0.086 (4) | −0.002 (3) | 0.043 (3) | 0.001 (3) |
C16 | 0.055 (2) | 0.039 (2) | 0.081 (3) | −0.0046 (18) | 0.004 (2) | 0.005 (2) |
C17 | 0.043 (2) | 0.038 (2) | 0.059 (3) | −0.0055 (17) | 0.0095 (18) | 0.0008 (19) |
C18 | 0.060 (3) | 0.079 (3) | 0.064 (3) | 0.020 (2) | 0.010 (2) | −0.016 (3) |
C19 | 0.043 (2) | 0.118 (5) | 0.076 (4) | 0.011 (3) | 0.009 (2) | 0.010 (3) |
C20 | 0.066 (3) | 0.060 (3) | 0.114 (5) | −0.018 (3) | −0.014 (3) | 0.002 (3) |
C21 | 0.113 (5) | 0.062 (3) | 0.126 (5) | 0.007 (3) | −0.023 (4) | −0.044 (4) |
C22 | 0.064 (3) | 0.062 (3) | 0.109 (4) | 0.012 (2) | 0.006 (3) | −0.021 (3) |
Ni1—N2 | 1.958 (3) | C7—H7C | 0.9600 |
Ni1—N1 | 1.963 (3) | C8—H8A | 0.9600 |
S1—P1 | 1.9674 (14) | C8—H8B | 0.9600 |
S2—P1 | 1.9661 (15) | C8—H8C | 0.9600 |
P1—O1 | 1.608 (3) | C9—C10 | 1.490 (6) |
P1—O2 | 1.613 (3) | C9—H9A | 0.9700 |
O1—C9 | 1.459 (4) | C9—H9B | 0.9700 |
O2—C16 | 1.432 (4) | C10—C15 | 1.374 (7) |
N1—C1 | 1.482 (4) | C10—C11 | 1.385 (6) |
N1—C6 | 1.509 (4) | C11—C12 | 1.400 (7) |
N1—H1 | 0.9100 | C11—H11 | 0.9300 |
N2—C2 | 1.493 (4) | C12—C13 | 1.366 (9) |
N2—C3 | 1.501 (4) | C12—H12 | 0.9300 |
N2—H2 | 0.9100 | C13—C14 | 1.354 (9) |
C1—C2 | 1.488 (5) | C13—H13 | 0.9300 |
C1—H1A | 0.9700 | C14—C15 | 1.363 (8) |
C1—H1B | 0.9700 | C14—H14 | 0.9300 |
C2—H2A | 0.9700 | C15—H15 | 0.9300 |
C2—H2B | 0.9700 | C16—C17 | 1.500 (5) |
C3—C4 | 1.510 (4) | C16—H16A | 0.9700 |
C3—C5 | 1.535 (4) | C16—H16B | 0.9700 |
C3—H3 | 0.9800 | C17—C18 | 1.369 (5) |
C4—C6i | 1.520 (4) | C17—C22 | 1.370 (6) |
C4—H4A | 0.9700 | C18—C19 | 1.388 (6) |
C4—H4B | 0.9700 | C18—H18 | 0.9300 |
C5—H5A | 0.9600 | C19—C20 | 1.332 (7) |
C5—H5B | 0.9600 | C19—H19 | 0.9300 |
C5—H5C | 0.9600 | C20—C21 | 1.366 (7) |
C6—C4i | 1.520 (4) | C20—H20 | 0.9300 |
C6—C7 | 1.528 (5) | C21—C22 | 1.376 (6) |
C6—C8 | 1.541 (5) | C21—H21 | 0.9300 |
C7—H7A | 0.9600 | C22—H22 | 0.9300 |
C7—H7B | 0.9600 | ||
N2—Ni1—N1 | 86.71 (11) | C6—C7—H7B | 109.5 |
N2i—Ni1—N1 | 93.29 (11) | H7A—C7—H7B | 109.5 |
O1—P1—O2 | 104.07 (15) | C6—C7—H7C | 109.5 |
O1—P1—S2 | 111.40 (12) | H7A—C7—H7C | 109.5 |
O2—P1—S2 | 103.65 (11) | H7B—C7—H7C | 109.5 |
O1—P1—S1 | 105.11 (11) | C6—C8—H8A | 109.5 |
O2—P1—S1 | 111.05 (11) | C6—C8—H8B | 109.5 |
S2—P1—S1 | 120.50 (7) | H8A—C8—H8B | 109.5 |
C9—O1—P1 | 119.1 (2) | C6—C8—H8C | 109.5 |
C16—O2—P1 | 120.7 (2) | H8A—C8—H8C | 109.5 |
C1—N1—C6 | 112.0 (2) | H8B—C8—H8C | 109.5 |
C1—N1—Ni1 | 108.7 (2) | O1—C9—C10 | 108.6 (3) |
C6—N1—Ni1 | 122.9 (2) | O1—C9—H9A | 110.0 |
C1—N1—H1 | 103.6 | C10—C9—H9A | 110.0 |
C6—N1—H1 | 103.6 | O1—C9—H9B | 110.0 |
Ni1—N1—H1 | 103.6 | C10—C9—H9B | 110.0 |
C2—N2—C3 | 110.1 (2) | H9A—C9—H9B | 108.3 |
C2—N2—Ni1 | 107.3 (2) | C15—C10—C11 | 118.4 (4) |
C3—N2—Ni1 | 121.11 (19) | C15—C10—C9 | 120.1 (4) |
C2—N2—H2 | 105.8 | C11—C10—C9 | 121.5 (4) |
C3—N2—H2 | 105.8 | C10—C11—C12 | 119.2 (5) |
Ni1—N2—H2 | 105.8 | C10—C11—H11 | 120.4 |
N1—C1—C2 | 108.0 (3) | C12—C11—H11 | 120.4 |
N1—C1—H1A | 110.1 | C13—C12—C11 | 120.1 (6) |
C2—C1—H1A | 110.1 | C13—C12—H12 | 119.9 |
N1—C1—H1B | 110.1 | C11—C12—H12 | 119.9 |
C2—C1—H1B | 110.1 | C14—C13—C12 | 120.6 (6) |
H1A—C1—H1B | 108.4 | C14—C13—H13 | 119.7 |
C1—C2—N2 | 107.9 (3) | C12—C13—H13 | 119.7 |
C1—C2—H2A | 110.1 | C13—C14—C15 | 119.5 (6) |
N2—C2—H2A | 110.1 | C13—C14—H14 | 120.2 |
C1—C2—H2B | 110.1 | C15—C14—H14 | 120.2 |
N2—C2—H2B | 110.1 | C14—C15—C10 | 122.2 (6) |
H2A—C2—H2B | 108.4 | C14—C15—H15 | 118.9 |
N2—C3—C4 | 110.0 (3) | C10—C15—H15 | 118.9 |
N2—C3—C5 | 112.4 (2) | O2—C16—C17 | 108.3 (3) |
C4—C3—C5 | 110.3 (3) | O2—C16—H16A | 110.0 |
N2—C3—H3 | 108.0 | C17—C16—H16A | 110.0 |
C4—C3—H3 | 108.0 | O2—C16—H16B | 110.0 |
C5—C3—H3 | 108.0 | C17—C16—H16B | 110.0 |
C3—C4—C6i | 117.4 (3) | H16A—C16—H16B | 108.4 |
C3—C4—H4A | 107.9 | C18—C17—C22 | 118.0 (4) |
C6i—C4—H4A | 107.9 | C18—C17—C16 | 121.3 (4) |
C3—C4—H4B | 107.9 | C22—C17—C16 | 120.6 (4) |
C6i—C4—H4B | 107.9 | C17—C18—C19 | 121.1 (4) |
H4A—C4—H4B | 107.2 | C17—C18—H18 | 119.4 |
C3—C5—H5A | 109.5 | C19—C18—H18 | 119.4 |
C3—C5—H5B | 109.5 | C20—C19—C18 | 119.8 (5) |
H5A—C5—H5B | 109.5 | C20—C19—H19 | 120.1 |
C3—C5—H5C | 109.5 | C18—C19—H19 | 120.1 |
H5A—C5—H5C | 109.5 | C19—C20—C21 | 120.3 (5) |
H5B—C5—H5C | 109.5 | C19—C20—H20 | 119.8 |
N1—C6—C4i | 108.0 (2) | C21—C20—H20 | 119.8 |
N1—C6—C7 | 109.6 (3) | C20—C21—C22 | 120.1 (5) |
C4i—C6—C7 | 111.1 (3) | C20—C21—H21 | 120.0 |
N1—C6—C8 | 109.6 (3) | C22—C21—H21 | 120.0 |
C4i—C6—C8 | 108.3 (3) | C17—C22—C21 | 120.6 (5) |
C7—C6—C8 | 110.3 (3) | C17—C22—H22 | 119.7 |
C6—C7—H7A | 109.5 | C21—C22—H22 | 119.7 |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1 | 0.91 | 2.61 | 3.390 (3) | 144 |
N2—H2···S2i | 0.91 | 2.50 | 3.394 (3) | 169 |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C16H36N4)](C14H14O2PS2)2 |
Mr | 961.88 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 290 |
a, b, c (Å) | 16.371 (5), 14.917 (5), 9.964 (4) |
β (°) | 103.11 (3) |
V (Å3) | 2369.9 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.70 |
Crystal size (mm) | 0.40 × 0.38 × 0.36 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.768, 0.787 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5571, 4393, 2880 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.127, 1.01 |
No. of reflections | 4393 |
No. of parameters | 275 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.52, −0.34 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1 | 0.91 | 2.61 | 3.390 (3) | 144.1 |
N2—H2···S2i | 0.91 | 2.50 | 3.394 (3) | 168.5 |
Symmetry code: (i) −x+1, −y+1, −z. |
Acknowledgements
Financial assistance from the Science and Technology Office of Zigong City, China (Project No. 06 G2045 and 07GX008) is gratefully acknowledged.
References
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Considerable interest in the chemistry of the O,O'-dialkyl dithiophosphate complexes of transition metal results from their value to industry, namely, as anti-oxidants, additives to lubricating oils, flotation reagents, insecticides(Liu et al.,1997;Li et al.,2006).We report here the synthesis and crystal structure of salt-type adduct [Ni(tet-a)][S2P(OCH2Ph)2]2 (tet-a=meso-5,5,7,12,12,14-hexamethyl- 1,4,8,11-tetraazacyclotetradecane, a tetradentate macrocyclic nitrogen base (Burchell et al.,2000; Ali et al.,2004 ))
The NiII in the complex cation [Ni(tet-a)]2+ lies on an inversion center and is coordinated by four nitrogen atoms of teteaaza macrocycle in undistorted square-planar geometry (Fig.1). The bond lengths and angles within the complex may be considered normal in comparison with the Cambridge Structural Database results (Allen, 2002).
The two O,O'- di(2-phenylmethyl) dithiophosphates act as counter-ions to balance the charge and they interact with the complex through N—H···S hydrogen bonds (Table 1).