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Acta Cryst. (2007). E63, m2168
https://doi.org/10.1107/S1600536807028760
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[1,4-Bis(diphenyl­phosphino)butane-κ2P,P′](dithio­carbonato-κ2S,S′)nickel(II)

M. V. Câmpian, I. Haiduc and R. F. Semeniuc
The Ni atom in the title complex, [Ni(COS2)(C28H28P2)], adopts a square-planar coordination geometry defined by two S atoms from the dithio­carbonate ligand and two P atoms from the diphosphine ligand. Mol­ecules are self-assembled into a supra­molecular array based upon weak inter­molecular C—H...O and C—H...π contacts.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028760/tk2161sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028760/tk2161Isup2.hkl
Contains datablock I

CCDC reference: 657596

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](Wave) = 0.000 Å
  • R factor = 0.038
  • wR factor = 0.097
  • Data-to-parameter ratio = 21.5

checkCIF/PLATON results

No syntax errors found




Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.685     1.000
            Tmin(prime) and Tmax expected:      0.661     0.785
            RR(prime) =      0.813
            Please check that your absorption correction is appropriate.


Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.785
            Tmax scaled      0.785 Tmin scaled      0.538


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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

The chemistry of nickel xanthates has been extensively investigated, resulting in a large number of crystal structures reported in the literature (Tiekink & Haiduc, 2005). In several cases, the reaction of nickel xanthates with dithiophosphinoethanes, via dealkylation of the xanthate ligand leads to formation of nickel dithiocarbonato complexes. Here, we report the crystal structure of one such complex, [Ni(S2CO)(dppb)] (I), where dppb is Ph2P(CH2)4PPh2, where dealkylation of the xanthate ion took place. A few complexes of the type [Ni(S2CO)L] [L = dppe = diphenylphosphinoethane (Trávnicek et al., 1996, Perpiñán et al., 1987, Haiduc et al., 2003), and L = dippe = diisopropylphosphinoethane (Tenorio et al., 1996)] are described in the literature, three of them characterized by X-Ray crystallography. The formation of dithiocarbonato complexes is sensitive to solvent used, molar ratio, reaction times and starting materials. The complex [Ni(S2CO)(dppe)] was obtained as an orange-red solid, starting from [Ni(S2COR)2] (R = Me, Et, Cy) with an excess of dppe in acetone/CHCl3 with long reaction times (Perpiñán et al., 1987) or starting from [Ni(S2COR)2] (R = iPr, Me, Et, MeOEt) in methylethylketone (Haiduc et al., 2003) or CHCl3 (Trávnicek et al., 1996) in a 1:1 molar ratio as orange crystals. The formation of a nickel dithiocarbonato complex also occurs when the complex [NiBr2(dippe)] is reacted with two equivalents of alkylxanthates (Tenorio et al., 1996) in acetone.

The nickel atom in I, Figure 1, adopts a distorded square planar coordination geometry, defined by two sulfur atoms from the dithiocarbonato ligand and two phosphorous atoms from dppb, with the metal deviation from S2P2 plane being -0.078 (2) Å. The dithiocarbonato ligand is more planar with an average deviation from the S2CO plane of 0.003 (2) Å. The Ni—S bond lengths in I are essentially equivalent (Table 1).

Complex molecules of (I) are self-assembled into a supramolecular array via two types of contacts. One contact is defined by C—H···O interactions along the a-axis. The contacts between adiacent molecules are C2a—H2a···O1 = 2.43 Å, C2a···O1 = 3.366 (3) Å, with the angle at H2a = 163° for symmetry code: 1 + x, y, z. The other interactions are of the type C—H···π, with C3—H3a···Cg1 [Cg1 is the centroid of ring C18—C23 at (1 - x, -y, 1 - z)] = 2.95 Å, and an angle of 164° at H3a. A view of the crystal packing is shown in Fig. 2.

Related literature top

For related literature, see: Haiduc et al. (2003); Perpiñán et al. (1987); Tenorio et al. (1996); Tiekink & Haiduc (2005); Trávnicek et al. (1996).

Experimental top

Complex I was prepared by two different methods:

1- To a solution of NiCl2 (0.118 g, 0.002 mol) in ethanol was added dppb (0.213 g, 0.002 mol). The cream precipitate which formed after 15 minutes was dried. A dichloromethane solution of resulting [NiCl2(dppb)] complex was treated with KS2COCH2C6H5 (0.111 g, 0.002 mol). The colour of solution changed to orange. Evaporation of the solution produced orange-red crystals.

2- To a solution of [Ni(S2COCH2C6H5)2] in dichloromethane was added dppb in molar rations 1:1 and 2:1. The colour of the solutions changed from green-brown to orange. In both cases, slow evaporation of the solutions produced orange-red crystals.

The crystals investigated in the present work were obtained by method 2.

IR (KBr): 1700 and 1606 ν(C=O) cm-1. M.p. 485 K (dec.).

Refinement top

Hydrogen atoms were placed in geometrically idealized positions and included as riding atoms with C—H = 0.93 - 0.97 Å, and with Uiso(H) = 1.2Uiso(C).

Structure description top

The chemistry of nickel xanthates has been extensively investigated, resulting in a large number of crystal structures reported in the literature (Tiekink & Haiduc, 2005). In several cases, the reaction of nickel xanthates with dithiophosphinoethanes, via dealkylation of the xanthate ligand leads to formation of nickel dithiocarbonato complexes. Here, we report the crystal structure of one such complex, [Ni(S2CO)(dppb)] (I), where dppb is Ph2P(CH2)4PPh2, where dealkylation of the xanthate ion took place. A few complexes of the type [Ni(S2CO)L] [L = dppe = diphenylphosphinoethane (Trávnicek et al., 1996, Perpiñán et al., 1987, Haiduc et al., 2003), and L = dippe = diisopropylphosphinoethane (Tenorio et al., 1996)] are described in the literature, three of them characterized by X-Ray crystallography. The formation of dithiocarbonato complexes is sensitive to solvent used, molar ratio, reaction times and starting materials. The complex [Ni(S2CO)(dppe)] was obtained as an orange-red solid, starting from [Ni(S2COR)2] (R = Me, Et, Cy) with an excess of dppe in acetone/CHCl3 with long reaction times (Perpiñán et al., 1987) or starting from [Ni(S2COR)2] (R = iPr, Me, Et, MeOEt) in methylethylketone (Haiduc et al., 2003) or CHCl3 (Trávnicek et al., 1996) in a 1:1 molar ratio as orange crystals. The formation of a nickel dithiocarbonato complex also occurs when the complex [NiBr2(dippe)] is reacted with two equivalents of alkylxanthates (Tenorio et al., 1996) in acetone.

The nickel atom in I, Figure 1, adopts a distorded square planar coordination geometry, defined by two sulfur atoms from the dithiocarbonato ligand and two phosphorous atoms from dppb, with the metal deviation from S2P2 plane being -0.078 (2) Å. The dithiocarbonato ligand is more planar with an average deviation from the S2CO plane of 0.003 (2) Å. The Ni—S bond lengths in I are essentially equivalent (Table 1).

Complex molecules of (I) are self-assembled into a supramolecular array via two types of contacts. One contact is defined by C—H···O interactions along the a-axis. The contacts between adiacent molecules are C2a—H2a···O1 = 2.43 Å, C2a···O1 = 3.366 (3) Å, with the angle at H2a = 163° for symmetry code: 1 + x, y, z. The other interactions are of the type C—H···π, with C3—H3a···Cg1 [Cg1 is the centroid of ring C18—C23 at (1 - x, -y, 1 - z)] = 2.95 Å, and an angle of 164° at H3a. A view of the crystal packing is shown in Fig. 2.

For related literature, see: Haiduc et al. (2003); Perpiñán et al. (1987); Tenorio et al. (1996); Tiekink & Haiduc (2005); Trávnicek et al. (1996).

Computing details top

Data collection: SMART NT (Bruker, 2001); cell refinement: SAINT-Plus NT (Bruker, 2001); data reduction: SAINT-Plus NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2000).

Figures top
[Figure 1] Fig. 1. The structures of I showing displacement ellipsoids at the 50% probability level and the atom-numbering scheme.
[Figure 2] Fig. 2. Supramolecular array in I. Dashed lines indicate C—H···O contacts. Colour code: Ni cyan, S yellow, O red, P purple, C grey and H green.
[1,4-Bis(diphenylphosphino)butane-κ2P,P'](dithiocarbonato-k2S,S')nickel(II) top
Crystal data top
[Ni(COS2)(C28H28P2)]Z = 2
Mr = 577.28F(000) = 600
Triclinic, P1Dx = 1.413 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.1860 (5) ÅCell parameters from 6076 reflections
b = 10.6926 (6) Åθ = 2.2–28.3°
c = 14.5447 (8) ŵ = 1.01 mm−1
α = 71.906 (1)°T = 294 K
β = 82.710 (1)°Block, orange-red
γ = 64.272 (1)°0.40 × 0.35 × 0.24 mm
V = 1356.46 (13) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer		6807 independent reflections
Radiation source: fine-focus sealed tube5803 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 28.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −13→13
Tmin = 0.685, Tmax = 1k = −14→14
16944 measured reflectionsl = −19→19
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0507P)2 + 0.2402P]
where P = (Fo2 + 2Fc2)/3
6807 reflections(Δ/σ)max = 0.001
316 parametersΔρmax = 0.50 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
[Ni(COS2)(C28H28P2)]γ = 64.272 (1)°
Mr = 577.28V = 1356.46 (13) Å3
Triclinic, P1Z = 2
a = 10.1860 (5) ÅMo Kα radiation
b = 10.6926 (6) ŵ = 1.01 mm−1
c = 14.5447 (8) ÅT = 294 K
α = 71.906 (1)°0.40 × 0.35 × 0.24 mm
β = 82.710 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		6807 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		5803 reflections with I > 2σ(I)
Tmin = 0.685, Tmax = 1Rint = 0.029
16944 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 1.02Δρmax = 0.50 e Å−3
6807 reflectionsΔρmin = −0.21 e Å−3
316 parameters
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
xyzUiso*/Ueq
Ni10.08348 (2)0.33684 (2)0.277861 (16)0.03010 (8)
P10.19635 (5)0.46982 (5)0.28031 (4)0.03368 (11)
P20.27605 (5)0.15608 (5)0.24566 (4)0.03491 (12)
S1−0.13030 (5)0.50629 (5)0.29704 (4)0.04401 (13)
S2−0.06149 (5)0.23653 (5)0.26890 (4)0.04244 (13)
C1−0.2082 (2)0.3967 (2)0.27981 (15)0.0412 (4)
C20.3590 (2)0.3826 (2)0.35932 (16)0.0452 (5)
H2A0.43680.40360.32210.054*
H2B0.33650.42680.41160.054*
C30.4157 (2)0.2194 (2)0.40317 (17)0.0505 (5)
H3A0.46640.19260.46320.061*
H3B0.33310.19440.41890.061*
C40.5177 (2)0.1305 (3)0.3392 (2)0.0583 (6)
H4A0.54650.02870.37320.070*
H4B0.60500.14790.32910.070*
C50.4550 (2)0.1611 (2)0.24049 (17)0.0493 (5)
H5A0.52300.09030.20910.059*
H5B0.44630.25600.20080.059*
C60.08675 (19)0.6338 (2)0.31755 (14)0.0367 (4)
C70.0233 (2)0.7690 (2)0.25106 (17)0.0500 (5)
H70.04010.77900.18540.060*
C8−0.0650 (3)0.8894 (2)0.28206 (19)0.0600 (6)
H8−0.10640.97970.23690.072*
C9−0.0918 (3)0.8768 (3)0.37830 (19)0.0565 (6)
H9−0.15120.95810.39850.068*
C10−0.0306 (3)0.7435 (3)0.44477 (18)0.0541 (5)
H10−0.04950.73450.51020.065*
C110.0589 (2)0.6225 (2)0.41530 (16)0.0464 (5)
H110.10070.53290.46110.056*
C120.2431 (2)0.5434 (2)0.15673 (15)0.0417 (4)
C130.1534 (3)0.5659 (3)0.08351 (17)0.0613 (6)
H130.07790.53650.09890.074*
C140.1743 (4)0.6314 (3)−0.0120 (2)0.0787 (8)
H140.11230.6472−0.06020.094*
C150.2856 (4)0.6724 (4)−0.0347 (2)0.0882 (10)
H150.30160.7143−0.09890.106*
C160.3741 (4)0.6524 (4)0.0360 (3)0.1005 (12)
H160.44940.68210.01940.121*
C170.3541 (3)0.5879 (3)0.1330 (2)0.0689 (7)
H170.41500.57540.18080.083*
C180.3102 (2)−0.0233 (2)0.32730 (14)0.0386 (4)
C190.2280 (2)−0.0386 (2)0.41011 (14)0.0407 (4)
H190.15410.04300.42360.049*
C200.2553 (2)−0.1748 (2)0.47298 (16)0.0492 (5)
H200.2004−0.18420.52880.059*
C210.3629 (3)−0.2957 (2)0.45310 (18)0.0560 (6)
H210.3801−0.38690.49510.067*
C220.4457 (3)−0.2825 (2)0.3713 (2)0.0621 (6)
H220.5190−0.36470.35820.074*
C230.4200 (2)−0.1472 (2)0.30866 (18)0.0546 (6)
H230.4765−0.13880.25350.066*
C240.2616 (2)0.1405 (2)0.12638 (15)0.0475 (5)
C250.2061 (3)0.0502 (3)0.1138 (2)0.0681 (7)
H250.1762−0.00620.16700.082*
C260.1950 (4)0.0438 (4)0.0202 (3)0.0967 (11)
H260.1580−0.01720.01110.116*
C270.2393 (4)0.1286 (5)−0.0583 (3)0.1049 (14)
H270.23440.1226−0.12010.126*
C280.2892 (4)0.2191 (5)−0.0459 (2)0.1035 (13)
H280.31600.2776−0.09950.124*
C290.3014 (3)0.2270 (3)0.04526 (19)0.0734 (8)
H290.33640.29060.05260.088*
O1−0.33527 (16)0.4258 (2)0.27567 (15)0.0696 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.02394 (12)0.02904 (13)0.03664 (13)−0.01032 (9)0.00049 (8)−0.00970 (9)
P10.0275 (2)0.0324 (2)0.0412 (3)−0.01285 (18)−0.00091 (18)−0.00970 (19)
P20.0288 (2)0.0326 (2)0.0407 (3)−0.01038 (18)0.00403 (18)−0.01192 (19)
S10.0282 (2)0.0381 (3)0.0661 (3)−0.01034 (19)0.0024 (2)−0.0213 (2)
S20.0338 (2)0.0407 (3)0.0592 (3)−0.0182 (2)0.0016 (2)−0.0192 (2)
C10.0298 (9)0.0465 (11)0.0481 (11)−0.0166 (8)0.0018 (8)−0.0140 (9)
C20.0343 (9)0.0436 (11)0.0592 (13)−0.0145 (8)−0.0108 (9)−0.0151 (9)
C30.0425 (11)0.0496 (12)0.0558 (13)−0.0184 (9)−0.0172 (9)−0.0049 (10)
C40.0321 (10)0.0457 (12)0.0901 (18)−0.0085 (9)−0.0163 (11)−0.0153 (12)
C50.0294 (9)0.0464 (12)0.0704 (15)−0.0142 (8)0.0104 (9)−0.0207 (10)
C60.0334 (9)0.0332 (9)0.0461 (10)−0.0159 (7)−0.0013 (7)−0.0114 (8)
C70.0576 (13)0.0377 (11)0.0494 (12)−0.0142 (10)−0.0059 (10)−0.0113 (9)
C80.0675 (15)0.0356 (11)0.0658 (15)−0.0083 (10)−0.0146 (12)−0.0134 (10)
C90.0517 (12)0.0475 (12)0.0709 (16)−0.0097 (10)−0.0062 (11)−0.0313 (11)
C100.0546 (13)0.0563 (14)0.0524 (13)−0.0196 (11)0.0044 (10)−0.0235 (11)
C110.0472 (11)0.0416 (11)0.0475 (12)−0.0181 (9)0.0018 (9)−0.0103 (9)
C120.0380 (9)0.0354 (10)0.0468 (11)−0.0136 (8)0.0058 (8)−0.0101 (8)
C130.0653 (15)0.0685 (16)0.0486 (13)−0.0325 (13)−0.0027 (11)−0.0069 (11)
C140.093 (2)0.081 (2)0.0474 (14)−0.0309 (17)−0.0022 (14)−0.0062 (13)
C150.088 (2)0.085 (2)0.0576 (17)−0.0255 (18)0.0222 (16)0.0002 (15)
C160.080 (2)0.116 (3)0.093 (2)−0.058 (2)0.0311 (19)0.000 (2)
C170.0552 (14)0.0801 (18)0.0725 (17)−0.0403 (14)0.0092 (12)−0.0088 (14)
C180.0360 (9)0.0305 (9)0.0461 (11)−0.0098 (7)−0.0020 (8)−0.0116 (8)
C190.0389 (10)0.0363 (10)0.0440 (11)−0.0121 (8)−0.0008 (8)−0.0125 (8)
C200.0513 (12)0.0445 (12)0.0476 (12)−0.0207 (10)−0.0042 (9)−0.0049 (9)
C210.0614 (14)0.0354 (11)0.0648 (15)−0.0176 (10)−0.0128 (11)−0.0043 (10)
C220.0583 (14)0.0345 (11)0.0785 (17)−0.0025 (10)−0.0045 (12)−0.0195 (11)
C230.0510 (12)0.0402 (11)0.0616 (14)−0.0086 (9)0.0100 (10)−0.0193 (10)
C240.0406 (10)0.0488 (12)0.0432 (11)−0.0065 (9)0.0021 (8)−0.0188 (9)
C250.0665 (16)0.0746 (18)0.0691 (17)−0.0239 (14)−0.0034 (13)−0.0351 (14)
C260.082 (2)0.114 (3)0.104 (3)−0.018 (2)−0.017 (2)−0.070 (2)
C270.083 (2)0.149 (4)0.064 (2)−0.011 (2)−0.0089 (17)−0.057 (2)
C280.101 (3)0.140 (4)0.0462 (16)−0.032 (3)0.0029 (16)−0.0237 (19)
C290.0768 (18)0.085 (2)0.0487 (14)−0.0296 (16)0.0097 (12)−0.0163 (13)
O10.0308 (7)0.0726 (12)0.1132 (15)−0.0208 (8)0.0029 (8)−0.0388 (11)
Geometric parameters (Å, º) top
Ni1—S12.1993 (5)C11—H110.9300
Ni1—S22.2042 (5)C12—C171.376 (3)
Ni1—P12.1922 (5)C12—C131.386 (3)
Ni1—P22.2000 (5)C13—C141.384 (3)
P1—C121.818 (2)C13—H130.9300
P1—C61.831 (2)C14—C151.354 (5)
P1—C21.8472 (19)C14—H140.9300
P2—C181.8225 (19)C15—C161.358 (5)
P2—C241.824 (2)C15—H150.9300
P2—C51.838 (2)C16—C171.397 (4)
S1—C11.762 (2)C16—H160.9300
S2—C11.754 (2)C17—H170.9300
C1—O11.198 (2)C18—C191.385 (3)
C2—C31.520 (3)C18—C231.393 (3)
C2—H2A0.9700C19—C201.386 (3)
C2—H2B0.9700C19—H190.9300
C3—C41.516 (3)C20—C211.370 (3)
C3—H3A0.9700C20—H200.9300
C3—H3B0.9700C21—C221.375 (3)
C4—C51.528 (3)C21—H210.9300
C4—H4A0.9700C22—C231.380 (3)
C4—H4B0.9700C22—H220.9300
C5—H5A0.9700C23—H230.9300
C5—H5B0.9700C24—C251.376 (4)
C6—C71.386 (3)C24—C291.393 (3)
C6—C111.392 (3)C25—C261.405 (4)
C7—C81.386 (3)C25—H250.9300
C7—H70.9300C26—C271.383 (6)
C8—C91.367 (3)C26—H260.9300
C8—H80.9300C27—C281.337 (6)
C9—C101.371 (3)C27—H270.9300
C9—H90.9300C28—C291.379 (4)
C10—C111.382 (3)C28—H280.9300
C10—H100.9300C29—H290.9300
S1—Ni1—S279.23 (2)C9—C10—H10119.7
S1—Ni1—P192.18 (2)C11—C10—H10119.7
S1—Ni1—P2170.09 (2)C10—C11—C6120.5 (2)
S2—Ni1—P1170.74 (2)C10—C11—H11119.8
S2—Ni1—P291.74 (2)C6—C11—H11119.8
P1—Ni1—P296.563 (19)C17—C12—C13118.7 (2)
C12—P1—C6102.21 (9)C17—C12—P1123.75 (19)
C12—P1—C2109.93 (10)C13—C12—P1117.32 (16)
C6—P1—C2102.47 (10)C14—C13—C12121.2 (2)
C12—P1—Ni1108.16 (7)C14—C13—H13119.4
C6—P1—Ni1115.82 (6)C12—C13—H13119.4
C2—P1—Ni1117.17 (7)C15—C14—C13119.5 (3)
C18—P2—C24104.29 (10)C15—C14—H14120.2
C18—P2—C5102.64 (9)C13—C14—H14120.2
C24—P2—C5102.18 (10)C14—C15—C16120.2 (3)
C18—P2—Ni1115.87 (6)C14—C15—H15119.9
C24—P2—Ni1111.50 (7)C16—C15—H15119.9
C5—P2—Ni1118.56 (7)C15—C16—C17121.3 (3)
C1—S1—Ni187.28 (7)C15—C16—H16119.4
C1—S2—Ni187.33 (7)C17—C16—H16119.4
O1—C1—S2126.94 (18)C12—C17—C16119.0 (3)
O1—C1—S1127.09 (18)C12—C17—H17120.5
S2—C1—S1105.97 (10)C16—C17—H17120.5
C3—C2—P1116.19 (14)C19—C18—C23118.72 (18)
C3—C2—H2A108.2C19—C18—P2120.30 (14)
P1—C2—H2A108.2C23—C18—P2120.98 (16)
C3—C2—H2B108.2C18—C19—C20120.33 (19)
P1—C2—H2B108.2C18—C19—H19119.8
H2A—C2—H2B107.4C20—C19—H19119.8
C4—C3—C2115.0 (2)C21—C20—C19120.2 (2)
C4—C3—H3A108.5C21—C20—H20119.9
C2—C3—H3A108.5C19—C20—H20119.9
C4—C3—H3B108.5C20—C21—C22120.3 (2)
C2—C3—H3B108.5C20—C21—H21119.9
H3A—C3—H3B107.5C22—C21—H21119.9
C3—C4—C5115.25 (17)C21—C22—C23120.0 (2)
C3—C4—H4A108.5C21—C22—H22120.0
C5—C4—H4A108.5C23—C22—H22120.0
C3—C4—H4B108.5C22—C23—C18120.5 (2)
C5—C4—H4B108.5C22—C23—H23119.7
H4A—C4—H4B107.5C18—C23—H23119.7
C4—C5—P2114.22 (15)C25—C24—C29119.0 (2)
C4—C5—H5A108.7C25—C24—P2121.76 (19)
P2—C5—H5A108.7C29—C24—P2119.2 (2)
C4—C5—H5B108.7C24—C25—C26119.6 (3)
P2—C5—H5B108.7C24—C25—H25120.2
H5A—C5—H5B107.6C26—C25—H25120.2
C7—C6—C11118.40 (19)C27—C26—C25119.7 (4)
C7—C6—P1122.11 (16)C27—C26—H26120.1
C11—C6—P1119.39 (15)C25—C26—H26120.1
C8—C7—C6120.3 (2)C28—C27—C26120.4 (3)
C8—C7—H7119.9C28—C27—H27119.8
C6—C7—H7119.9C26—C27—H27119.8
C9—C8—C7120.8 (2)C27—C28—C29120.9 (4)
C9—C8—H8119.6C27—C28—H28119.5
C7—C8—H8119.6C29—C28—H28119.5
C8—C9—C10119.5 (2)C28—C29—C24120.4 (3)
C8—C9—H9120.2C28—C29—H29119.8
C10—C9—H9120.2C24—C29—H29119.8
C9—C10—C11120.5 (2)
S1—Ni1—P1—C12−103.16 (7)C6—P1—C12—C1780.7 (2)
P2—Ni1—P1—C1272.16 (7)C2—P1—C12—C17−27.5 (2)
S1—Ni1—P1—C610.79 (7)Ni1—P1—C12—C17−156.61 (19)
P2—Ni1—P1—C6−173.89 (7)C6—P1—C12—C13−93.94 (19)
S1—Ni1—P1—C2131.98 (9)C2—P1—C12—C13157.80 (18)
P2—Ni1—P1—C2−52.70 (9)Ni1—P1—C12—C1328.74 (19)
P1—Ni1—P2—C18127.04 (7)C17—C12—C13—C140.2 (4)
S2—Ni1—P2—C18−57.06 (8)P1—C12—C13—C14175.1 (2)
P1—Ni1—P2—C24−113.90 (8)C12—C13—C14—C151.0 (5)
S2—Ni1—P2—C2462.00 (8)C13—C14—C15—C16−1.5 (5)
P1—Ni1—P2—C54.30 (9)C14—C15—C16—C170.8 (6)
S2—Ni1—P2—C5−179.80 (9)C13—C12—C17—C16−0.9 (4)
P1—Ni1—S1—C1173.66 (7)P1—C12—C17—C16−175.5 (2)
S2—Ni1—S1—C1−2.87 (7)C15—C16—C17—C120.4 (5)
S1—Ni1—S2—C12.88 (7)C24—P2—C18—C19−130.28 (17)
P2—Ni1—S2—C1−173.00 (7)C5—P2—C18—C19123.45 (17)
Ni1—S2—C1—O1175.8 (2)Ni1—P2—C18—C19−7.34 (19)
Ni1—S2—C1—S1−3.67 (9)C24—P2—C18—C2350.6 (2)
Ni1—S1—C1—O1−175.8 (2)C5—P2—C18—C23−55.7 (2)
Ni1—S1—C1—S23.68 (9)Ni1—P2—C18—C23173.53 (16)
C12—P1—C2—C3−114.16 (18)C23—C18—C19—C200.1 (3)
C6—P1—C2—C3137.74 (17)P2—C18—C19—C20−179.03 (16)
Ni1—P1—C2—C39.8 (2)C18—C19—C20—C21−0.7 (3)
P1—C2—C3—C484.9 (2)C19—C20—C21—C220.8 (4)
C2—C3—C4—C5−57.5 (3)C20—C21—C22—C23−0.3 (4)
C3—C4—C5—P2−50.8 (2)C21—C22—C23—C18−0.2 (4)
C18—P2—C5—C4−55.40 (18)C19—C18—C23—C220.3 (3)
C24—P2—C5—C4−163.29 (16)P2—C18—C23—C22179.49 (19)
Ni1—P2—C5—C473.73 (17)C18—P2—C24—C2532.2 (2)
C12—P1—C6—C718.83 (19)C5—P2—C24—C25138.8 (2)
C2—P1—C6—C7132.71 (17)Ni1—P2—C24—C25−93.57 (19)
Ni1—P1—C6—C7−98.49 (16)C18—P2—C24—C29−150.84 (19)
C12—P1—C6—C11−164.81 (16)C5—P2—C24—C29−44.2 (2)
C2—P1—C6—C11−50.93 (17)Ni1—P2—C24—C2983.41 (19)
Ni1—P1—C6—C1177.87 (16)C29—C24—C25—C262.0 (4)
C11—C6—C7—C80.3 (3)P2—C24—C25—C26178.9 (2)
P1—C6—C7—C8176.71 (18)C24—C25—C26—C27−0.2 (5)
C6—C7—C8—C9−0.5 (4)C25—C26—C27—C28−1.7 (5)
C7—C8—C9—C100.0 (4)C26—C27—C28—C291.8 (6)
C8—C9—C10—C110.7 (4)C27—C28—C29—C24−0.1 (5)
C9—C10—C11—C6−0.8 (3)C25—C24—C29—C28−1.8 (4)
C7—C6—C11—C100.3 (3)P2—C24—C29—C28−178.9 (2)
P1—C6—C11—C10−176.18 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O1i0.972.433.366 (3)163
C3—H3A···Cg1ii0.972.95?164
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula[Ni(COS2)(C28H28P2)]
Mr577.28
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)10.1860 (5), 10.6926 (6), 14.5447 (8)
α, β, γ (°)71.906 (1), 82.710 (1), 64.272 (1)
V (Å3)1356.46 (13)
Z2
Radiation typeMo Kα
µ (mm−1)1.01
Crystal size (mm)0.40 × 0.35 × 0.24
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.685, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections		16944, 6807, 5803
Rint0.029
(sin θ/λ)max (Å−1)0.671
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.097, 1.02
No. of reflections6807
No. of parameters316
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.50, −0.21

Computer programs: SMART NT (Bruker, 2001), SAINT-Plus NT (Bruker, 2001), SAINT-Plus NT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2000).

Selected geometric parameters (Å, º) top
Ni1—S12.1993 (5)S1—C11.762 (2)
Ni1—S22.2042 (5)S2—C11.754 (2)
Ni1—P12.1922 (5)C1—O11.198 (2)
Ni1—P22.2000 (5)
S1—Ni1—S279.23 (2)S2—Ni1—P1170.74 (2)
S1—Ni1—P192.18 (2)S2—Ni1—P291.74 (2)
S1—Ni1—P2170.09 (2)P1—Ni1—P296.563 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O1i0.972.433.366 (3)163
C3—H3A···Cg1ii0.972.95?164
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1.
 

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