trans-Bis(4-methoxy­thio­phenolato-κS)bis­(trimethyl­phosphine-κP)nickel(II)

Cao, R.; Wang, Q.; Sun, H.

doi:10.1107/S1600536807067591

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m279

doi:10.1107/S1600536807067591

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trans-Bis(4-methoxythiophenolato-κS)bis(trimethylphosphine-κP)nickel(II)

Ruixia Cao,^a Qibao Wang ^a and Hongjian Sun ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Shanda Nanlu 27, Jinan 250100, People's Republic of China
^*Correspondence e-mail: hjsun@sdu.edu.cn

(Received 5 November 2007; accepted 18 December 2007; online 4 January 2008)

The title compound, [Ni(C₇H₇OS)₂(C₃H₉P)₂], was obtained as a product of the reaction of [NiMe₂(PMe₃)₃] with two molar equivalents of 4-methoxythiophenol in diethyl ether. The compound is stable in the air for several hours, but rapidly decomposes at room temperature in solution. The Ni atom displays a square-planar coordination with two P-donor atoms lying in trans positions. The benzene rings of the thiophenolate ligands are almost perpendicular to the square coordination plane, making dihedral angles of 80.43 (4) and 72.60 (4)°.

Related literature

For the crystal structures of related diphenolato-nickel compounds, see: Klein et al. (1998 ). For synthetic details, see: Klein & Karsch (1972 ).

Experimental

Crystal data

[Ni(C₇H₇OS)₂(C₃H₉P)₂]
M_r = 489.23
Monoclinic, P 2₁ /c
a = 14.022 (3) Å
b = 15.983 (3) Å
c = 10.758 (2) Å
β = 100.93 (3)°
V = 2367.3 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.14 mm⁻¹
T = 273 (2) K
0.30 × 0.24 × 0.21 mm

Data collection

Bruker P4 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.725, T_max = 0.795
14644 measured reflections
5103 independent reflections
4078 reflections with I > 2σ(I)
R_int = 0.040
14954 standard reflections every 6 reflections intensity decay: 30%

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.00
5103 reflections
372 parameters
All H-atom parameters refined
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—P1	2.2121 (7)
Ni1—P2	2.2224 (7)
Ni1—S2	2.2261 (9)
Ni1—S1	2.2288 (9)

P1—Ni1—P2	178.07 (2)
P1—Ni1—S2	87.01 (3)
P2—Ni1—S2	93.17 (3)
P1—Ni1—S1	92.17 (3)
P2—Ni1—S1	87.67 (3)
S2—Ni1—S1	178.85 (2)

Data collection: XSCANS (Siemens, 1996 ); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2001 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067591/fi2053sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807067591/fi2053Isup2.hkl

checkCIF report

Comment top

In the title molecule (Fig.1) the nickel atom is coordinated in a square-planar geometry by two P atoms of trimethylphosphine groups and two S atoms of thiophenol groups. The phenyl rings of the thiophenlato ligands are almost perpendicular to the square coordination plane (angles 80.43 (4)° and 72.60 (4)°). Similar crystal structures have been reported in the literature, e.g. Bis(2-tert-butyl-4-methylphenolato)bis(trimethylphosphane)nickel and Bis(2-tert-butyl-6-methylphenolato)bis(trimethylphosphane)nickel (Klein et al.(1998)). The bond lengths and angles of these compounds are similar to those in the title compound.

Related literature top

For the crystal structures of related diphenolato–nickel compounds, see: Klein et al. 1998). For synthetic details, see: Klein & Karsch (1972).

Experimental top

Dimethyltris(trimethylphosphine)nickel was prepared according to the literature (Klein & Karsch (1972)). Other chemicals were used by purchased. To the solution of NiMe₂(PMe₃)₃ (1.0 g, 3.15 mmol) in 50 ml of diethyl ether was added 4-methoxythiophenol (0.884 g, 6.30 mmol) at -80 °C, a dark red suspension formed rapidly. After stirring at room temperature for 16 h the reaction solution was filtrated, then the red solid residue was extracted with THF (50 ml). Crystallization from ether and THF at 4 °C afforded dark red crystals suitable for X-ray diffraction analysis. (yield: 0.89 g, 57.8%, m. p.: 135 °C).

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: SHELXTL (Sheldrick, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

Fig. 1. The molecular structure of (I), with a 30% probability displacement ellipsoids for non-H atoms.

[trans-Bis(4-methoxythiophenolato-κS)bis(trimethylphosphine-κP)nickel(II) top

Crystal data top

[Ni(C₇H₇OS)₂(C₃H₉P)₂]	F(000) = 1032
M_r = 489.23	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1843 reflections
a = 14.022 (3) Å	θ = 2.4–24.3°
b = 15.983 (3) Å	µ = 1.14 mm⁻¹
c = 10.758 (2) Å	T = 273 K
β = 100.93 (3)°	Cubic, dark red
V = 2367.3 (8) Å³	0.30 × 0.24 × 0.21 mm
Z = 4

Data collection top

Bruker P4 diffractometer	4078 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 27.1°, θ_min = 1.5°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −20→20
T_min = 0.725, T_max = 0.795	l = −13→13
14644 measured reflections	14954 standard reflections every 6 reflections
5103 independent reflections	intensity decay: 30%

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) = 0.085	All H-atom parameters refined
S = 1.00	w = 1/[σ²(F_o²) + (0.0526P)²] where P = (F_o² + 2F_c²)/3
5103 reflections	(Δ/σ)_max = 0.001
372 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Ni(C₇H₇OS)₂(C₃H₉P)₂]	V = 2367.3 (8) Å³
M_r = 489.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.022 (3) Å	µ = 1.14 mm⁻¹
b = 15.983 (3) Å	T = 273 K
c = 10.758 (2) Å	0.30 × 0.24 × 0.21 mm
β = 100.93 (3)°

Data collection top

Bruker P4 diffractometer	4078 reflections with I > 2σ(I)
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	R_int = 0.040
T_min = 0.725, T_max = 0.795	14954 standard reflections every 6 reflections
14644 measured reflections	intensity decay: 30%
5103 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.085	All H-atom parameters refined
S = 1.00	Δρ_max = 0.34 e Å⁻³
5103 reflections	Δρ_min = −0.47 e Å⁻³
372 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

	x	y	z	U_iso*/U_eq
Ni1	0.257048 (17)	0.016260 (16)	0.74629 (2)	0.03027 (9)
P1	0.37880 (4)	0.08109 (3)	0.68296 (5)	0.03426 (13)
P2	0.13706 (4)	−0.05297 (3)	0.80892 (5)	0.03389 (13)
S1	0.17664 (4)	0.00061 (3)	0.54812 (5)	0.03656 (13)
S2	0.33803 (4)	0.03453 (3)	0.94334 (5)	0.03455 (12)
C1	0.24429 (14)	−0.07893 (12)	0.48988 (19)	0.0322 (4)
C2	0.30721 (15)	−0.13200 (13)	0.56961 (19)	0.0345 (4)
C3	0.35857 (15)	−0.19580 (13)	0.52267 (19)	0.0336 (4)
C4	0.34651 (14)	−0.20757 (12)	0.39280 (19)	0.0319 (4)
C5	0.28431 (15)	−0.15531 (13)	0.31149 (19)	0.0334 (4)
C6	0.23405 (15)	−0.09207 (13)	0.35826 (19)	0.0318 (4)
C7	0.4551 (2)	−0.32462 (15)	0.4172 (3)	0.0473 (6)
C8	0.25968 (14)	0.10267 (12)	1.00678 (18)	0.0317 (4)
C9	0.19724 (15)	0.15744 (13)	0.9314 (2)	0.0349 (4)
C10	0.13341 (16)	0.20890 (13)	0.9820 (2)	0.0352 (4)
C11	0.13282 (14)	0.20600 (12)	1.11072 (19)	0.0330 (4)
C12	0.19604 (15)	0.15232 (13)	1.18851 (19)	0.0344 (4)
C13	0.25869 (15)	0.10109 (13)	1.13772 (19)	0.0330 (4)
C14	0.00536 (19)	0.30705 (15)	1.0914 (3)	0.0465 (6)
C15	0.49677 (17)	0.03403 (16)	0.7405 (3)	0.0439 (5)
C16	0.3913 (2)	0.18866 (15)	0.7388 (3)	0.0465 (5)
C17	0.3817 (2)	0.0948 (2)	0.5153 (2)	0.0527 (6)
C18	0.01701 (18)	−0.00824 (17)	0.7602 (3)	0.0492 (6)
C19	0.1249 (2)	−0.15763 (16)	0.7437 (3)	0.0489 (6)
C20	0.1384 (3)	−0.0739 (2)	0.9760 (3)	0.0594 (7)
O1	0.39280 (12)	−0.26858 (9)	0.33592 (14)	0.0417 (4)
O2	0.07266 (11)	0.25359 (10)	1.16992 (14)	0.0409 (3)
H8	0.3030 (17)	0.0637 (14)	1.193 (2)	0.037 (6)*
H4	0.1928 (17)	−0.0562 (14)	0.305 (2)	0.036 (6)*
H2	0.4020 (17)	−0.2288 (14)	0.581 (2)	0.037 (6)*
H6	0.0932 (18)	0.2463 (15)	0.926 (2)	0.042 (6)*
H1	0.3157 (18)	−0.1256 (15)	0.658 (2)	0.045 (7)*
H7	0.1979 (17)	0.1481 (13)	1.278 (2)	0.038 (6)*
H3	0.2763 (18)	−0.1623 (15)	0.226 (2)	0.043 (6)*
H30	0.083 (2)	−0.1094 (17)	0.983 (3)	0.060 (8)*
H21	0.444 (2)	0.1243 (17)	0.506 (3)	0.064 (8)*
H5	0.2010 (18)	0.1621 (15)	0.843 (2)	0.047 (7)*
H22	0.3789 (19)	0.0424 (18)	0.477 (3)	0.047 (7)*
H24	−0.028 (2)	−0.0478 (17)	0.788 (3)	0.061 (8)*
H15	0.506 (2)	0.0290 (18)	0.822 (3)	0.064 (9)*
H27	0.065 (2)	−0.1831 (17)	0.755 (3)	0.061 (8)*
H16	0.544 (2)	0.0681 (17)	0.715 (3)	0.059 (8)*
H12	−0.031 (2)	0.3322 (17)	1.149 (3)	0.059 (8)*
H9	0.5112 (18)	−0.2937 (15)	0.477 (2)	0.045 (6)*
H25	0.004 (2)	−0.0024 (19)	0.673 (3)	0.072 (10)*
H18	0.387 (2)	0.1897 (17)	0.826 (3)	0.059 (8)*
H13	−0.0356 (19)	0.2742 (16)	1.023 (3)	0.046 (7)*
H28	0.123 (2)	−0.1555 (17)	0.655 (3)	0.061 (8)*
H19	0.341 (2)	0.2181 (19)	0.694 (3)	0.070 (9)*
H14	0.038 (2)	0.3483 (18)	1.049 (3)	0.060 (8)*
H31	0.130 (2)	−0.021 (2)	1.020 (3)	0.078 (10)*
H29	0.183 (2)	−0.1915 (19)	0.785 (3)	0.076 (9)*
H32	0.190 (2)	−0.1022 (19)	1.005 (3)	0.066 (10)*
H20	0.455 (2)	0.2127 (17)	0.728 (3)	0.062 (8)*
H17	0.500 (2)	−0.0226 (18)	0.701 (3)	0.059 (8)*
H10	0.4198 (19)	−0.3535 (16)	0.469 (3)	0.051 (7)*
H11	0.480 (2)	−0.3626 (17)	0.361 (3)	0.062 (8)*
H26	0.010 (2)	0.047 (2)	0.799 (3)	0.066 (9)*
H23	0.327 (2)	0.125 (2)	0.477 (3)	0.073 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02676 (14)	0.03814 (15)	0.02594 (14)	0.00280 (10)	0.00507 (11)	−0.00110 (9)
P1	0.0296 (3)	0.0426 (3)	0.0310 (3)	0.0011 (2)	0.0065 (2)	0.0020 (2)
P2	0.0300 (3)	0.0403 (3)	0.0314 (3)	−0.0006 (2)	0.0058 (2)	0.0005 (2)
S1	0.0313 (3)	0.0491 (3)	0.0280 (3)	0.0076 (2)	0.0023 (2)	−0.0026 (2)
S2	0.0304 (3)	0.0442 (3)	0.0280 (2)	0.0055 (2)	0.0028 (2)	−0.0019 (2)
C1	0.0274 (9)	0.0401 (10)	0.0288 (10)	−0.0031 (8)	0.0045 (8)	−0.0007 (8)
C2	0.0355 (11)	0.0437 (11)	0.0241 (9)	0.0010 (8)	0.0048 (9)	−0.0020 (8)
C3	0.0340 (10)	0.0375 (10)	0.0287 (10)	−0.0003 (8)	0.0046 (9)	0.0015 (8)
C4	0.0340 (10)	0.0319 (9)	0.0305 (10)	−0.0039 (8)	0.0079 (9)	−0.0022 (7)
C5	0.0357 (11)	0.0401 (10)	0.0243 (10)	−0.0054 (8)	0.0055 (9)	−0.0017 (8)
C6	0.0303 (10)	0.0370 (10)	0.0273 (10)	−0.0026 (8)	0.0033 (8)	0.0034 (8)
C7	0.0602 (16)	0.0377 (11)	0.0441 (13)	0.0093 (11)	0.0102 (13)	−0.0008 (10)
C8	0.0311 (10)	0.0364 (10)	0.0278 (10)	−0.0005 (8)	0.0057 (8)	−0.0015 (8)
C9	0.0369 (11)	0.0408 (11)	0.0277 (10)	0.0021 (8)	0.0076 (9)	0.0013 (8)
C10	0.0374 (11)	0.0354 (10)	0.0326 (11)	0.0038 (8)	0.0060 (9)	0.0022 (8)
C11	0.0315 (10)	0.0344 (9)	0.0342 (11)	−0.0038 (8)	0.0090 (9)	−0.0078 (8)
C12	0.0364 (11)	0.0413 (11)	0.0257 (10)	−0.0048 (8)	0.0066 (9)	−0.0030 (8)
C13	0.0329 (10)	0.0361 (10)	0.0286 (10)	−0.0010 (8)	0.0021 (9)	0.0011 (8)
C14	0.0482 (14)	0.0390 (12)	0.0538 (15)	0.0080 (10)	0.0136 (12)	−0.0038 (11)
C15	0.0336 (11)	0.0498 (13)	0.0508 (15)	0.0038 (10)	0.0144 (11)	0.0081 (11)
C16	0.0448 (14)	0.0432 (12)	0.0521 (15)	0.0023 (10)	0.0106 (12)	0.0040 (11)
C17	0.0517 (16)	0.0705 (18)	0.0376 (13)	−0.0125 (14)	0.0124 (12)	0.0036 (12)
C18	0.0362 (12)	0.0544 (14)	0.0597 (17)	0.0063 (10)	0.0161 (12)	0.0100 (12)
C19	0.0460 (14)	0.0430 (12)	0.0597 (17)	−0.0040 (11)	0.0148 (13)	−0.0049 (11)
C20	0.0605 (18)	0.075 (2)	0.0420 (14)	−0.0214 (16)	0.0091 (14)	0.0093 (13)
O1	0.0503 (9)	0.0424 (8)	0.0319 (8)	0.0087 (7)	0.0061 (7)	−0.0055 (6)
O2	0.0388 (8)	0.0495 (8)	0.0353 (8)	0.0066 (7)	0.0091 (7)	−0.0084 (6)

Geometric parameters (Å, º) top

Ni1—P1	2.2121 (7)	C9—H5	0.96 (2)
Ni1—P2	2.2224 (7)	C10—C11	1.387 (3)
Ni1—S2	2.2261 (9)	C10—H6	0.96 (3)
Ni1—S1	2.2288 (9)	C11—O2	1.378 (2)
P1—C15	1.816 (2)	C11—C12	1.393 (3)
P1—C16	1.819 (3)	C12—C13	1.387 (3)
P1—C17	1.825 (3)	C12—H7	0.96 (2)
P2—C19	1.809 (3)	C13—H8	0.98 (2)
P2—C18	1.812 (3)	C14—O2	1.425 (3)
P2—C20	1.825 (3)	C14—H12	0.97 (3)
S1—C1	1.770 (2)	C14—H13	0.99 (3)
S2—C8	1.7729 (19)	C14—H14	0.97 (3)
C1—C2	1.395 (3)	C15—H15	0.86 (3)
C1—C6	1.412 (3)	C15—H16	0.94 (3)
C2—C3	1.397 (3)	C15—H17	1.01 (3)
C2—H1	0.94 (3)	C16—H18	0.95 (3)
C3—C4	1.388 (3)	C16—H19	0.91 (3)
C3—H2	0.95 (2)	C16—H20	1.00 (3)
C4—O1	1.377 (2)	C17—H21	1.02 (3)
C4—C5	1.391 (3)	C17—H22	0.93 (3)
C5—C6	1.381 (3)	C17—H23	0.93 (3)
C5—H3	0.91 (3)	C18—H24	0.98 (3)
C6—H4	0.93 (2)	C18—H25	0.92 (4)
C7—O1	1.428 (3)	C18—H26	0.99 (3)
C7—H9	1.04 (3)	C19—H27	0.96 (3)
C7—H10	0.94 (3)	C19—H28	0.95 (3)
C7—H11	0.97 (3)	C19—H29	1.01 (3)
C8—C9	1.386 (3)	C20—H30	0.97 (3)
C8—C13	1.412 (3)	C20—H31	0.99 (4)
C9—C10	1.400 (3)	C20—H32	0.86 (3)

P1—Ni1—P2	178.07 (2)	O2—C11—C10	124.26 (19)
P1—Ni1—S2	87.01 (3)	O2—C11—C12	115.96 (18)
P2—Ni1—S2	93.17 (3)	C10—C11—C12	119.78 (18)
P1—Ni1—S1	92.17 (3)	C13—C12—C11	120.36 (18)
P2—Ni1—S1	87.67 (3)	C13—C12—H7	117.0 (14)
S2—Ni1—S1	178.85 (2)	C11—C12—H7	122.6 (14)
C15—P1—C16	104.76 (13)	C12—C13—C8	120.63 (19)
C15—P1—C17	101.37 (14)	C12—C13—H8	120.1 (13)
C16—P1—C17	101.21 (14)	C8—C13—H8	119.2 (13)
C15—P1—Ni1	114.04 (8)	O2—C14—H12	104.1 (17)
C16—P1—Ni1	111.87 (8)	O2—C14—H13	110.3 (14)
C17—P1—Ni1	121.57 (10)	H12—C14—H13	113 (2)
C19—P2—C18	103.82 (14)	O2—C14—H14	111.5 (18)
C19—P2—C20	101.25 (15)	H12—C14—H14	112 (2)
C18—P2—C20	101.07 (16)	H13—C14—H14	106 (2)
C19—P2—Ni1	111.32 (9)	P1—C15—H15	110 (2)
C18—P2—Ni1	115.54 (9)	P1—C15—H16	108.0 (17)
C20—P2—Ni1	121.54 (10)	H15—C15—H16	112 (3)
C1—S1—Ni1	102.20 (7)	P1—C15—H17	109.9 (17)
C8—S2—Ni1	101.87 (7)	H15—C15—H17	110 (3)
C2—C1—C6	117.29 (18)	H16—C15—H17	107 (2)
C2—C1—S1	122.53 (15)	P1—C16—H18	108.8 (17)
C6—C1—S1	120.16 (16)	P1—C16—H19	107 (2)
C1—C2—C3	122.05 (19)	H18—C16—H19	109 (3)
C1—C2—H1	119.9 (15)	P1—C16—H20	111.0 (16)
C3—C2—H1	118.0 (15)	H18—C16—H20	109 (2)
C4—C3—C2	119.3 (2)	H19—C16—H20	111 (2)
C4—C3—H2	121.8 (14)	P1—C17—H21	109.3 (17)
C2—C3—H2	118.8 (14)	P1—C17—H22	108.9 (17)
O1—C4—C3	124.43 (19)	H21—C17—H22	110 (2)
O1—C4—C5	115.97 (17)	P1—C17—H23	109.3 (19)
C3—C4—C5	119.60 (18)	H21—C17—H23	112 (3)
C6—C5—C4	120.87 (18)	H22—C17—H23	108 (3)
C6—C5—H3	118.9 (15)	P2—C18—H24	106.1 (17)
C4—C5—H3	120.2 (15)	P2—C18—H25	109 (2)
C5—C6—C1	120.84 (19)	H24—C18—H25	111 (3)
C5—C6—H4	121.8 (14)	P2—C18—H26	113.3 (18)
C1—C6—H4	117.3 (14)	H24—C18—H26	108 (2)
O1—C7—H9	112.5 (14)	H25—C18—H26	109 (3)
O1—C7—H10	110.2 (16)	P2—C19—H27	111.2 (16)
H9—C7—H10	107 (2)	P2—C19—H28	109.9 (17)
O1—C7—H11	105.1 (17)	H27—C19—H28	106 (3)
H9—C7—H11	111 (2)	P2—C19—H29	108.5 (18)
H10—C7—H11	111 (2)	H27—C19—H29	112 (2)
C9—C8—C13	118.05 (18)	H28—C19—H29	109 (2)
C9—C8—S2	122.12 (15)	P2—C20—H30	108.9 (17)
C13—C8—S2	119.82 (16)	P2—C20—H31	110 (2)
C8—C9—C10	121.55 (19)	H30—C20—H31	107 (2)
C8—C9—H5	118.6 (15)	P2—C20—H32	107 (2)
C10—C9—H5	119.8 (15)	H30—C20—H32	107 (3)
C11—C10—C9	119.6 (2)	H31—C20—H32	117 (3)
C11—C10—H6	122.6 (14)	C4—O1—C7	117.19 (17)
C9—C10—H6	117.8 (14)	C11—O2—C14	116.84 (17)

Experimental details

Crystal data
Chemical formula	[Ni(C₇H₇OS)₂(C₃H₉P)₂]
M_r	489.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	14.022 (3), 15.983 (3), 10.758 (2)
β (°)	100.93 (3)
V (Å³)	2367.3 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.14
Crystal size (mm)	0.30 × 0.24 × 0.21

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.725, 0.795
No. of measured, independent and observed [I > 2σ(I)] reflections	14644, 5103, 4078
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.085, 1.00
No. of reflections	5103
No. of parameters	372
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.47

Computer programs: XSCANS (Siemens, 1996), SHELXTL (Sheldrick, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).

Selected geometric parameters (Å, º) top

Ni1—P1	2.2121 (7)	Ni1—S2	2.2261 (9)
Ni1—P2	2.2224 (7)	Ni1—S1	2.2288 (9)

P1—Ni1—P2	178.07 (2)	P1—Ni1—S1	92.17 (3)
P1—Ni1—S2	87.01 (3)	P2—Ni1—S1	87.67 (3)
P2—Ni1—S2	93.17 (3)	S2—Ni1—S1	178.85 (2)

Acknowledgements

This work was supported by the NSFC (grant Nos. 20572062 and 20372042).

References

Klein, H.-F., Dal, A., Jung, T., Braun, S., Roehr, C., Floerke, U. & Haupt, H.-J. (1998). Eur. J. Inorg. Chem. pp. 621–627. CrossRef Google Scholar
Klein, H.-F. & Karsch, H. H. (1972). Chem. Ber. 105, 2628–2636. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2001). SHELXTL. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Siemens (1996). XSCANS. Version 2.2. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar