supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2009). E65, m156    [ doi:10.1107/S1600536808044280 ]

[1,2-Bis(diphenylphosphino)ethane-[kappa]2P,P'](2-carboxylatothiophenolato-[kappa]2O,S)nickel(II) methanol solvate

J. Miao, F. Li, H. Chen, D. Wang and Y. Nie

Abstract top

In the title complex, [Ni(C7H4O2S)(C26H24P2)]·CH3OH, the nickel(II) centre adopts an approximately square-planar geometry, with the Ni atom coordinating to the S and O atoms of the bidentate thiosalicylate ligand and the two P atoms of the chelating Ph2PCH2CH2PPh2 ligand. There is hydrogen bonding between the methanol solvent molecule and the carbonyl O atom of the thiosalicylate ligand.

Comment top

The synthesis and crystal structure of [(dppe)Ni(tsal)] (where dppe is Ph2PCH2CH2PPh2 and tsal is thiosalicylato) have been described by McCaffrey et al. (1997) by a reaction of NiCl2(dppe) and tsalH2 in the presence of pyridine, and also by Kang et al. (1998) via a similar reaction of NiCl2, dppe and thiosalicylate. We have recently obtained the same complex as a methanol solvate when NiCl2(dppe) was reacted with thiosalicylic acid in the presence of NaOH as a base.

As shown in Fig. 1, the coordination geometry around the nickel center is approximately square planar. The sum of the bond angles around the Ni atom is 359.92°, with the trans P—Ni—S and P—Ni—O angles being 172.70 and 178.81°, respectively, Table 1, while in related structures the corresponding values were found to be 361.45, 170.99 and 170.73° (McCaffrey et al., 1997), and 358.4, 166.0, 173.0°, (Kang et al., 1998) respectively. These indicate that in the present structure the P2OS unit is slightly more planar. As expected, the Ni1—P2 bond length (opposite to S, 2.2114 (10) Å) is found to be longer than that for Ni1—P1 (opposite to O, 2.1378 (11) Å), due to the different trans influence of the S and O atoms. Strong O3—H3···O2i [i = x, -y + 1/2, z - 1/2] hydrogen bonding (2.697 Å) is observed between the methanol solvate molecule and the carbonyl O atom of the thiosalicylato group, Table 2.

Related literature top

For previous preparations and structures of the non-solvated complex, see: Kang et al. (1998); McCaffrey et al. (1997).

Experimental top

Thiosalicylic acid (32 mg, 0.2 mmol) was added to a solution of NaOH (0.2 mmol) in methanol (2 ml) to give a slightly yellow solution. This was transferred dropwise to a suspension of NiCl2(dppe) (53 mg, 0.1 mmol) in CH3CN (3 ml). After stirring for 10 min, a deep-red solution formed, from which red crystals (55 mg, 85%) were grown on standing at room temperature. IR (KBr): ν = 3399, 3053, 1596, 1435, 1351, 1102, 746, 690, 531 cm -1.

Refinement top

All H atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso = 1.2Ueq(C) for aromatic, 0.97 Å, Uiso = 1.2Ueq(C) for CH2, 0.96 Å, Uiso = 1.5Ueq(C) for CH3 atoms and 0.82 Å, Uiso = 1.5Ueq(O) for the OH groups.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure, with atom labels and 25% probability displacement ellipsoids for non-H atoms.
[1,2-Bis(diphenylphosphino)ethane-κ2P,P'](2- carboxylatothiophenolato-κ2O,S)nickel(II) methanol solvate top
Crystal data top
[Ni(C7H4O2S)(C26H24P2)]·CH4OF(000) = 1336
Mr = 641.31Dx = 1.367 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3936 reflections
a = 13.9229 (15) Åθ = 2.3–25.0°
b = 11.6244 (10) ŵ = 0.83 mm−1
c = 19.553 (2) ÅT = 293 K
β = 100.085 (2)°Needle, red
V = 3115.6 (6) Å30.48 × 0.37 × 0.32 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		5484 independent reflections
Radiation source: fine-focus sealed tube3538 reflections with I > 2σ(I)
graphiteRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −16→16
Tmin = 0.693, Tmax = 0.778k = −13→13
14599 measured reflectionsl = −23→13
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0402P)2 + 2.3624P]
where P = (Fo2 + 2Fc2)/3
5484 reflections(Δ/σ)max = 0.001
370 parametersΔρmax = 0.42 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
[Ni(C7H4O2S)(C26H24P2)]·CH4OV = 3115.6 (6) Å3
Mr = 641.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.9229 (15) ŵ = 0.83 mm−1
b = 11.6244 (10) ÅT = 293 K
c = 19.553 (2) Å0.48 × 0.37 × 0.32 mm
β = 100.085 (2)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		5484 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		3538 reflections with I > 2σ(I)
Tmin = 0.693, Tmax = 0.778Rint = 0.032
14599 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.117Δρmax = 0.42 e Å−3
S = 1.10Δρmin = −0.26 e Å−3
5484 reflectionsAbsolute structure: ?
370 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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 > 2sigma(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
Ni10.77033 (3)0.40652 (4)0.63023 (2)0.04036 (15)
O10.75357 (19)0.2853 (2)0.69264 (13)0.0507 (7)
O20.7291 (2)0.2026 (3)0.78879 (16)0.0759 (9)
O30.8043 (4)0.5076 (4)0.3236 (2)0.1394 (18)
H30.78700.44080.31550.209*
P10.79225 (7)0.54152 (9)0.56033 (5)0.0436 (3)
P20.81015 (7)0.28485 (8)0.55286 (5)0.0411 (2)
S10.74372 (7)0.54170 (9)0.70171 (5)0.0510 (3)
C10.7130 (3)0.2809 (3)0.7457 (2)0.0475 (9)
C20.6393 (3)0.3695 (3)0.75551 (18)0.0438 (9)
C30.6457 (3)0.4843 (3)0.73642 (19)0.0471 (9)
C40.5722 (3)0.5591 (4)0.7480 (2)0.0725 (13)
H40.57630.63660.73690.087*
C50.4931 (4)0.5208 (5)0.7755 (3)0.0915 (17)
H50.44370.57180.78120.110*
C60.4872 (3)0.4087 (5)0.7944 (3)0.0829 (15)
H60.43380.38270.81260.099*
C70.5615 (3)0.3340 (4)0.7861 (2)0.0611 (11)
H70.55930.25840.80140.073*
C80.8596 (3)0.4831 (3)0.4959 (2)0.0527 (10)
H8A0.85360.53410.45610.063*
H8B0.92820.47590.51590.063*
C90.8175 (3)0.3661 (3)0.47359 (19)0.0496 (10)
H9A0.85910.32650.44630.060*
H9B0.75310.37440.44550.060*
C100.6782 (3)0.5982 (3)0.5114 (2)0.0523 (10)
C110.6009 (3)0.6230 (4)0.5438 (3)0.0807 (15)
H110.60770.61270.59160.097*
C120.5135 (3)0.6628 (5)0.5074 (4)0.0972 (19)
H120.46290.68230.53060.117*
C130.5019 (4)0.6734 (5)0.4376 (4)0.096 (2)
H130.44220.69710.41250.116*
C140.5748 (5)0.6504 (5)0.4049 (3)0.109 (2)
H140.56600.65920.35690.130*
C150.6655 (4)0.6127 (5)0.4412 (3)0.0929 (18)
H150.71650.59780.41750.111*
C160.8670 (3)0.6616 (3)0.59772 (19)0.0490 (10)
C170.8367 (3)0.7736 (4)0.5916 (2)0.0642 (12)
H170.77440.79130.56820.077*
C180.8993 (4)0.8608 (4)0.6203 (3)0.0812 (15)
H180.87880.93700.61570.097*
C190.9905 (4)0.8357 (5)0.6552 (3)0.0829 (16)
H191.03170.89460.67450.099*
C201.0213 (3)0.7247 (5)0.6618 (2)0.0753 (14)
H201.08370.70780.68520.090*
C210.9599 (3)0.6372 (4)0.6338 (2)0.0642 (12)
H210.98090.56130.63910.077*
C220.9319 (3)0.2273 (3)0.58174 (18)0.0441 (9)
C230.9691 (3)0.2240 (5)0.6509 (2)0.0847 (17)
H230.93370.25540.68260.102*
C241.0588 (4)0.1746 (5)0.6744 (3)0.100 (2)
H241.08240.17130.72190.119*
C251.1126 (3)0.1313 (4)0.6301 (3)0.0783 (15)
H251.17430.10160.64640.094*
C261.0760 (4)0.1313 (5)0.5615 (3)0.105 (2)
H261.11180.09910.53040.125*
C270.9856 (3)0.1791 (5)0.5375 (2)0.0917 (18)
H270.96100.17820.49010.110*
C280.7366 (3)0.1591 (3)0.52550 (19)0.0438 (9)
C290.6959 (4)0.0986 (4)0.5731 (2)0.0695 (13)
H290.70370.12340.61890.083*
C300.6425 (4)−0.0007 (5)0.5523 (3)0.0901 (17)
H300.6144−0.04160.58460.108*
C310.6312 (3)−0.0381 (4)0.4863 (3)0.0742 (14)
H310.5960−0.10510.47360.089*
C320.6703 (4)0.0206 (4)0.4382 (3)0.0748 (14)
H320.6624−0.00580.39260.090*
C330.7224 (3)0.1206 (4)0.4574 (2)0.0672 (13)
H330.74800.16230.42420.081*
C340.8066 (7)0.5619 (7)0.2643 (4)0.192 (4)
H34A0.77060.63250.26330.288*
H34B0.77780.51410.22620.288*
H34C0.87300.57840.26060.288*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0375 (3)0.0465 (3)0.0377 (3)0.0053 (2)0.0082 (2)−0.0006 (2)
O10.0646 (17)0.0471 (16)0.0446 (15)0.0164 (13)0.0210 (14)0.0023 (12)
O20.087 (2)0.073 (2)0.074 (2)0.0221 (18)0.0314 (18)0.0313 (18)
O30.217 (5)0.109 (3)0.090 (3)−0.041 (3)0.021 (3)−0.015 (3)
P10.0375 (5)0.0488 (6)0.0436 (6)0.0021 (4)0.0048 (5)0.0033 (5)
P20.0407 (5)0.0480 (6)0.0349 (5)0.0083 (4)0.0079 (4)0.0013 (4)
S10.0550 (6)0.0490 (6)0.0518 (6)−0.0048 (5)0.0168 (5)−0.0098 (5)
C10.044 (2)0.049 (2)0.048 (2)−0.0002 (18)0.0054 (19)−0.002 (2)
C20.040 (2)0.057 (3)0.034 (2)−0.0029 (18)0.0049 (17)−0.0051 (18)
C30.045 (2)0.056 (3)0.041 (2)0.0072 (19)0.0099 (18)−0.0073 (19)
C40.076 (3)0.070 (3)0.077 (3)0.026 (3)0.030 (3)0.001 (3)
C50.070 (3)0.108 (5)0.106 (4)0.032 (3)0.042 (3)0.002 (4)
C60.059 (3)0.109 (5)0.089 (4)−0.003 (3)0.035 (3)−0.007 (3)
C70.058 (3)0.071 (3)0.058 (3)−0.006 (2)0.019 (2)−0.006 (2)
C80.047 (2)0.064 (3)0.048 (2)0.006 (2)0.0114 (19)0.010 (2)
C90.042 (2)0.068 (3)0.040 (2)0.0117 (19)0.0102 (17)0.0093 (19)
C100.047 (2)0.047 (2)0.058 (3)0.0043 (19)−0.005 (2)0.001 (2)
C110.047 (3)0.103 (4)0.091 (4)0.011 (3)0.007 (3)0.029 (3)
C120.043 (3)0.110 (5)0.134 (5)0.009 (3)0.003 (3)0.032 (4)
C130.069 (4)0.080 (4)0.120 (5)0.011 (3)−0.037 (4)−0.013 (4)
C140.119 (5)0.120 (5)0.070 (4)0.053 (4)−0.033 (4)−0.012 (3)
C150.096 (4)0.112 (4)0.064 (3)0.045 (3)−0.004 (3)−0.003 (3)
C160.046 (2)0.056 (3)0.046 (2)−0.0077 (19)0.0098 (19)0.001 (2)
C170.073 (3)0.055 (3)0.064 (3)−0.005 (2)0.009 (2)0.006 (2)
C180.108 (4)0.054 (3)0.084 (4)−0.017 (3)0.026 (3)−0.008 (3)
C190.087 (4)0.097 (4)0.068 (3)−0.041 (3)0.023 (3)−0.014 (3)
C200.058 (3)0.102 (4)0.064 (3)−0.021 (3)0.008 (2)−0.009 (3)
C210.053 (3)0.075 (3)0.063 (3)−0.007 (2)0.006 (2)−0.003 (2)
C220.042 (2)0.051 (2)0.040 (2)0.0077 (17)0.0103 (17)0.0026 (18)
C230.062 (3)0.142 (5)0.048 (3)0.045 (3)0.003 (2)−0.013 (3)
C240.074 (3)0.162 (6)0.057 (3)0.055 (4)−0.004 (3)−0.007 (3)
C250.053 (3)0.110 (4)0.070 (3)0.028 (3)0.005 (3)0.014 (3)
C260.087 (4)0.167 (6)0.067 (3)0.073 (4)0.034 (3)0.023 (4)
C270.080 (3)0.151 (5)0.046 (3)0.061 (4)0.014 (2)0.010 (3)
C280.040 (2)0.049 (2)0.042 (2)0.0079 (18)0.0068 (17)0.0008 (19)
C290.096 (4)0.062 (3)0.054 (3)−0.010 (3)0.023 (3)−0.004 (2)
C300.122 (5)0.077 (4)0.078 (4)−0.033 (3)0.038 (3)0.002 (3)
C310.072 (3)0.058 (3)0.088 (4)−0.010 (2)0.004 (3)−0.003 (3)
C320.082 (3)0.071 (3)0.066 (3)−0.011 (3)−0.003 (3)−0.013 (3)
C330.075 (3)0.074 (3)0.053 (3)−0.010 (3)0.011 (2)−0.003 (2)
C340.264 (11)0.185 (9)0.123 (6)−0.099 (8)0.025 (7)0.050 (6)
Geometric parameters (Å, °) top
Ni1—O11.905 (3)C14—C151.406 (7)
Ni1—P12.1378 (11)C14—H140.9300
Ni1—S12.1775 (11)C15—H150.9300
Ni1—P22.2114 (10)C16—C171.367 (5)
O1—C11.267 (4)C16—C211.390 (5)
O2—C11.234 (4)C17—C181.390 (6)
O3—C341.326 (7)C17—H170.9300
O3—H30.8200C18—C191.363 (7)
P1—C161.817 (4)C18—H180.9300
P1—C101.827 (4)C19—C201.358 (7)
P1—C81.828 (4)C19—H190.9300
P2—C281.811 (4)C20—C211.378 (6)
P2—C221.818 (4)C20—H200.9300
P2—C91.833 (4)C21—H210.9300
S1—C31.759 (4)C22—C271.360 (5)
C1—C21.490 (5)C22—C231.362 (5)
C2—C71.389 (5)C23—C241.378 (6)
C2—C31.393 (5)C23—H230.9300
C3—C41.391 (5)C24—C251.339 (6)
C4—C51.381 (6)C24—H240.9300
C4—H40.9300C25—C261.348 (6)
C5—C61.360 (7)C25—H250.9300
C5—H50.9300C26—C271.381 (6)
C6—C71.381 (6)C26—H260.9300
C6—H60.9300C27—H270.9300
C7—H70.9300C28—C291.366 (5)
C8—C91.514 (5)C28—C331.386 (5)
C8—H8A0.9700C29—C301.394 (6)
C8—H8B0.9700C29—H290.9300
C9—H9A0.9700C30—C311.345 (7)
C9—H9B0.9700C30—H300.9300
C10—C151.363 (6)C31—C321.352 (6)
C10—C111.372 (6)C31—H310.9300
C11—C121.379 (6)C32—C331.387 (6)
C11—H110.9300C32—H320.9300
C12—C131.351 (8)C33—H330.9300
C12—H120.9300C34—H34A0.9600
C13—C141.318 (8)C34—H34B0.9600
C13—H130.9300C34—H34C0.9600
O1—Ni1—P1178.81 (8)C13—C14—C15121.1 (6)
O1—Ni1—S193.94 (8)C13—C14—H14119.4
P1—Ni1—S186.56 (4)C15—C14—H14119.4
O1—Ni1—P292.22 (8)C10—C15—C14119.6 (5)
P1—Ni1—P287.20 (4)C10—C15—H15120.2
S1—Ni1—P2172.70 (4)C14—C15—H15120.2
C1—O1—Ni1132.6 (3)C17—C16—C21119.0 (4)
C34—O3—H3109.5C17—C16—P1123.4 (3)
C16—P1—C10108.55 (18)C21—C16—P1117.7 (3)
C16—P1—C8103.64 (18)C16—C17—C18119.8 (4)
C10—P1—C8106.08 (19)C16—C17—H17120.1
C16—P1—Ni1116.27 (13)C18—C17—H17120.1
C10—P1—Ni1113.02 (14)C19—C18—C17120.6 (5)
C8—P1—Ni1108.39 (13)C19—C18—H18119.7
C28—P2—C22104.04 (17)C17—C18—H18119.7
C28—P2—C9106.18 (18)C20—C19—C18120.1 (5)
C22—P2—C9105.40 (17)C20—C19—H19119.9
C28—P2—Ni1121.47 (12)C18—C19—H19119.9
C22—P2—Ni1110.78 (12)C19—C20—C21120.0 (5)
C9—P2—Ni1107.84 (13)C19—C20—H20120.0
C3—S1—Ni1101.81 (13)C21—C20—H20120.0
O2—C1—O1122.4 (4)C20—C21—C16120.5 (5)
O2—C1—C2118.0 (4)C20—C21—H21119.7
O1—C1—C2119.6 (4)C16—C21—H21119.7
C7—C2—C3119.5 (4)C27—C22—C23117.7 (4)
C7—C2—C1117.2 (4)C27—C22—P2122.7 (3)
C3—C2—C1123.4 (3)C23—C22—P2119.4 (3)
C4—C3—C2118.2 (4)C22—C23—C24120.5 (4)
C4—C3—S1117.9 (3)C22—C23—H23119.8
C2—C3—S1123.9 (3)C24—C23—H23119.8
C5—C4—C3121.3 (5)C25—C24—C23121.2 (5)
C5—C4—H4119.3C25—C24—H24119.4
C3—C4—H4119.3C23—C24—H24119.4
C6—C5—C4120.3 (5)C24—C25—C26119.2 (4)
C6—C5—H5119.8C24—C25—H25120.4
C4—C5—H5119.8C26—C25—H25120.4
C5—C6—C7119.3 (5)C25—C26—C27120.1 (5)
C5—C6—H6120.4C25—C26—H26120.0
C7—C6—H6120.4C27—C26—H26120.0
C6—C7—C2121.3 (4)C22—C27—C26121.3 (4)
C6—C7—H7119.4C22—C27—H27119.4
C2—C7—H7119.4C26—C27—H27119.4
C9—C8—P1108.2 (3)C29—C28—C33118.8 (4)
C9—C8—H8A110.1C29—C28—P2119.7 (3)
P1—C8—H8A110.1C33—C28—P2121.5 (3)
C9—C8—H8B110.1C28—C29—C30119.4 (4)
P1—C8—H8B110.1C28—C29—H29120.3
H8A—C8—H8B108.4C30—C29—H29120.3
C8—C9—P2107.2 (3)C31—C30—C29121.0 (5)
C8—C9—H9A110.3C31—C30—H30119.5
P2—C9—H9A110.3C29—C30—H30119.5
C8—C9—H9B110.3C30—C31—C32120.7 (5)
P2—C9—H9B110.3C30—C31—H31119.7
H9A—C9—H9B108.5C32—C31—H31119.7
C15—C10—C11117.7 (4)C31—C32—C33119.4 (5)
C15—C10—P1121.3 (4)C31—C32—H32120.3
C11—C10—P1120.9 (3)C33—C32—H32120.3
C10—C11—C12121.6 (5)C28—C33—C32120.7 (4)
C10—C11—H11119.2C28—C33—H33119.6
C12—C11—H11119.2C32—C33—H33119.6
C13—C12—C11119.4 (6)O3—C34—H34A109.5
C13—C12—H12120.3O3—C34—H34B109.5
C11—C12—H12120.3H34A—C34—H34B109.5
C14—C13—C12120.4 (5)O3—C34—H34C109.5
C14—C13—H13119.8H34A—C34—H34C109.5
C12—C13—H13119.8H34B—C34—H34C109.5
P1—Ni1—O1—C1134 (4)C16—P1—C10—C11−85.0 (4)
S1—Ni1—O1—C119.1 (3)C8—P1—C10—C11164.1 (4)
P2—Ni1—O1—C1−164.8 (3)Ni1—P1—C10—C1145.5 (4)
O1—Ni1—P1—C16−70 (4)C15—C10—C11—C12−0.9 (8)
S1—Ni1—P1—C1644.69 (15)P1—C10—C11—C12−178.2 (4)
P2—Ni1—P1—C16−131.52 (15)C10—C11—C12—C132.7 (9)
O1—Ni1—P1—C10163 (4)C11—C12—C13—C14−2.8 (9)
S1—Ni1—P1—C10−81.83 (15)C12—C13—C14—C151.0 (10)
P2—Ni1—P1—C10101.96 (15)C11—C10—C15—C14−0.9 (8)
O1—Ni1—P1—C846 (4)P1—C10—C15—C14176.4 (4)
S1—Ni1—P1—C8160.88 (14)C13—C14—C15—C100.9 (9)
P2—Ni1—P1—C8−15.33 (14)C10—P1—C16—C173.2 (4)
O1—Ni1—P2—C2849.42 (16)C8—P1—C16—C17115.6 (4)
P1—Ni1—P2—C28−131.62 (14)Ni1—P1—C16—C17−125.5 (3)
S1—Ni1—P2—C28−162.9 (3)C10—P1—C16—C21−176.3 (3)
O1—Ni1—P2—C22−73.03 (15)C8—P1—C16—C21−63.8 (3)
P1—Ni1—P2—C22105.93 (13)Ni1—P1—C16—C2155.0 (3)
S1—Ni1—P2—C2274.6 (4)C21—C16—C17—C181.0 (6)
O1—Ni1—P2—C9172.11 (15)P1—C16—C17—C18−178.4 (3)
P1—Ni1—P2—C9−8.93 (13)C16—C17—C18—C19−0.6 (7)
S1—Ni1—P2—C9−40.2 (4)C17—C18—C19—C200.4 (8)
O1—Ni1—S1—C3−41.42 (15)C18—C19—C20—C21−0.7 (8)
P1—Ni1—S1—C3139.66 (13)C19—C20—C21—C161.1 (7)
P2—Ni1—S1—C3171.0 (3)C17—C16—C21—C20−1.2 (6)
Ni1—O1—C1—O2−162.4 (3)P1—C16—C21—C20178.2 (3)
Ni1—O1—C1—C220.7 (5)C28—P2—C22—C2767.9 (4)
O2—C1—C2—C7−32.1 (5)C9—P2—C22—C27−43.6 (5)
O1—C1—C2—C7144.9 (4)Ni1—P2—C22—C27−160.0 (4)
O2—C1—C2—C3147.1 (4)C28—P2—C22—C23−107.1 (4)
O1—C1—C2—C3−35.9 (5)C9—P2—C22—C23141.4 (4)
C7—C2—C3—C4−1.0 (6)Ni1—P2—C22—C2325.0 (4)
C1—C2—C3—C4179.8 (4)C27—C22—C23—C240.8 (8)
C7—C2—C3—S1176.4 (3)P2—C22—C23—C24176.1 (5)
C1—C2—C3—S1−2.8 (5)C22—C23—C24—C251.7 (10)
Ni1—S1—C3—C4−141.0 (3)C23—C24—C25—C26−3.2 (10)
Ni1—S1—C3—C241.6 (3)C24—C25—C26—C272.2 (10)
C2—C3—C4—C5−2.0 (7)C23—C22—C27—C26−1.8 (8)
S1—C3—C4—C5−179.6 (4)P2—C22—C27—C26−176.9 (5)
C3—C4—C5—C62.3 (8)C25—C26—C27—C220.3 (10)
C4—C5—C6—C70.5 (8)C22—P2—C28—C2986.9 (4)
C5—C6—C7—C2−3.6 (7)C9—P2—C28—C29−162.1 (3)
C3—C2—C7—C63.8 (6)Ni1—P2—C28—C29−38.7 (4)
C1—C2—C7—C6−177.0 (4)C22—P2—C28—C33−91.5 (4)
C16—P1—C8—C9166.6 (3)C9—P2—C28—C3319.4 (4)
C10—P1—C8—C9−79.2 (3)Ni1—P2—C28—C33142.9 (3)
Ni1—P1—C8—C942.5 (3)C33—C28—C29—C300.9 (7)
P1—C8—C9—P2−49.1 (3)P2—C28—C29—C30−177.5 (4)
C28—P2—C9—C8168.2 (2)C28—C29—C30—C310.5 (8)
C22—P2—C9—C8−81.8 (3)C29—C30—C31—C32−0.8 (9)
Ni1—P2—C9—C836.5 (3)C30—C31—C32—C33−0.2 (8)
C16—P1—C10—C1597.7 (4)C29—C28—C33—C32−2.0 (6)
C8—P1—C10—C15−13.1 (4)P2—C28—C33—C32176.5 (3)
Ni1—P1—C10—C15−131.7 (4)C31—C32—C33—C281.6 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.821.882.697 (5)171
Symmetry codes: (i) x, −y+1/2, z−1/2.
Table 1
Selected geometric parameters (Å, °) top
Ni1—O11.905 (3)Ni1—P22.2114 (10)
Ni1—P12.1378 (11)O1—C11.267 (4)
Ni1—S12.1775 (11)O2—C11.234 (4)
O1—Ni1—P1178.81 (8)O1—Ni1—P292.22 (8)
O1—Ni1—S193.94 (8)P1—Ni1—P287.20 (4)
P1—Ni1—S186.56 (4)S1—Ni1—P2172.70 (4)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.821.882.697 (5)171
Symmetry codes: (i) x, −y+1/2, z−1/2.
Acknowledgements top

The authors thank the University of Jinan (B0604) for support of this work.

references
References top

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Kang, B.-S., Chen, Z.-N., Gao, H.-R., Zhou, Z.-Y., Wu, B.-M., Mak, T. M. C. & Lin, Z. (1998). Acta Chim. Sin. 56, 58–67.

McCaffrey, L. J., Henderson, W., Nicholson, B. K., Mackay, J. E. & Dinger, M. B. (1997). J. Chem. Soc. Dalton Trans. pp. 2577–2586.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.