Bis[O-methyl (4-eth-oxy-phen-yl)dithio-phospho-nato-κ(2) S,S']nickel(II).

In the title compound, [Ni(C9H12O2PS2)2], the Ni(II) atom resides on an inversion center and is coordinated by four S atoms [Ni-S = 2.2328 (4) and 2.2455 (3) Å] in a distorted square-planar geometry [S-Ni-S = 88.443 (13) and 91.557 (13)°]. In the crystal, mol-ecules related by translation in [110] are linked into chains via weak C-H⋯O inter-actions. The crystal packing exhibits short inter-molecular S⋯S contacts of 3.3366 (5) Å.

Related literature

For information on dithio­phospho­nate compounds, see: Van Zyl & Fackler (2000 ▶); Van Zyl (2010 ▶); Van Zyl & Woollins (2012 ▶). For related structures of nickel(II) dithio­phospho­nate complexes, see: Hartung (1967 ▶); Liu et al. (2004 ▶); Gray et al. (2004 ▶); Aragoni et al. (2007 ▶); Arca et al. (1997 ▶); Özcan et al. (2002 ▶).

Experimental

Crystal data

[Ni(C9H12O2PS2)2]

M = 553.26

Monoclinic,

a = 13.5866 (5) Å

b = 6.4212 (2) Å

c = 14.1047 (5) Å

β = 109.389 (2)°

V = 1160.74 (7) Å3

Z = 2

Mo Kα radiation

μ = 1.36 mm−1

T = 173 K

0.43 × 0.31 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.593, T max = 0.737

19824 measured reflections

2850 independent reflections

2609 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.062

S = 1.07

2850 reflections

135 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2008 ▶); 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: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046314/cv5358sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046314/cv5358Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C9H12O2PS2)2]	F(000) = 572
Mr = 553.26	Dx = 1.583 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19824 reflections
a = 13.5866 (5) Å	θ = 2.9–28.4°
b = 6.4212 (2) Å	µ = 1.36 mm−1
c = 14.1047 (5) Å	T = 173 K
β = 109.389 (2)°	Block, purple
V = 1160.74 (7) Å3	0.43 × 0.31 × 0.24 mm
Z = 2

Bruker SMART APEXII CCD diffractometer	2850 independent reflections
Radiation source: fine-focus sealed tube	2609 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 28.4°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→17
Tmin = 0.593, Tmax = 0.737	k = −8→8
19824 measured reflections	l = −18→18

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0281P)2 + 0.7956P] where P = (Fo2 + 2Fc2)/3
2850 reflections	(Δ/σ)max = 0.001
135 parameters	Δρmax = 0.56 e Å−3
2 restraints	Δρmin = −0.44 e Å−3

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
C1	0.70393 (11)	0.8288 (2)	0.85131 (10)	0.0149 (3)
C2	0.68704 (11)	0.6590 (2)	0.90614 (11)	0.0175 (3)
H2	0.7398	0.5564	0.9306	0.021*
C3	0.59371 (12)	0.6398 (2)	0.92488 (12)	0.0196 (3)
H3	0.5823	0.5237	0.9617	0.024*
C4	0.51619 (11)	0.7913 (2)	0.88969 (11)	0.0167 (3)
C5	0.53108 (12)	0.9588 (3)	0.83320 (12)	0.0202 (3)
H5	0.4777	1.0598	0.8075	0.024*
C6	0.62531 (12)	0.9759 (3)	0.81507 (12)	0.0211 (3)
H6	0.6362	1.0905	0.7771	0.025*
C7	0.34352 (11)	0.9068 (2)	0.87693 (12)	0.0199 (3)
H7A	0.3191	0.9120	0.8026	0.024*
H7B	0.3662	1.0480	0.9033	0.024*
C8	0.25769 (12)	0.8303 (3)	0.91356 (13)	0.0258 (3)
H8A	0.2401	0.6862	0.8915	0.039*
H8B	0.1959	0.9186	0.8859	0.039*
H8C	0.2812	0.8364	0.9871	0.039*
C9	0.88481 (12)	0.8281 (3)	0.67579 (12)	0.0243 (3)
H9A	0.9184	0.9650	0.6891	0.036*
H9B	0.8562	0.8052	0.6031	0.036*
H9C	0.9363	0.7197	0.7065	0.036*
O1	0.42818 (8)	0.76065 (18)	0.91366 (8)	0.0210 (2)
O2	0.80067 (8)	0.81965 (17)	0.71841 (7)	0.0172 (2)
P1	0.82716 (3)	0.87053 (6)	0.83456 (3)	0.01290 (9)
S1	0.88018 (3)	1.16115 (5)	0.87163 (3)	0.01505 (9)
S2	0.94269 (3)	0.69659 (5)	0.92450 (3)	0.01547 (9)
Ni1	1.0000	1.0000	1.0000	0.01236 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0126 (6)	0.0163 (7)	0.0142 (6)	−0.0026 (5)	0.0024 (5)	−0.0008 (5)
C2	0.0168 (7)	0.0162 (7)	0.0186 (7)	0.0021 (5)	0.0050 (5)	0.0025 (6)
C3	0.0200 (7)	0.0181 (7)	0.0218 (7)	0.0007 (6)	0.0085 (6)	0.0061 (6)
C4	0.0156 (6)	0.0187 (7)	0.0157 (6)	−0.0013 (6)	0.0050 (5)	−0.0007 (6)
C5	0.0152 (7)	0.0194 (7)	0.0246 (7)	0.0024 (6)	0.0050 (6)	0.0065 (6)
C6	0.0177 (7)	0.0201 (7)	0.0252 (7)	0.0005 (6)	0.0067 (6)	0.0088 (6)
C7	0.0171 (7)	0.0192 (7)	0.0239 (7)	0.0027 (6)	0.0074 (6)	−0.0006 (6)
C8	0.0209 (7)	0.0271 (9)	0.0324 (9)	0.0015 (6)	0.0127 (7)	−0.0004 (7)
C9	0.0219 (7)	0.0328 (9)	0.0212 (7)	0.0004 (7)	0.0113 (6)	−0.0025 (7)
O1	0.0176 (5)	0.0231 (6)	0.0251 (5)	0.0041 (4)	0.0107 (4)	0.0069 (5)
O2	0.0164 (5)	0.0212 (5)	0.0133 (5)	−0.0019 (4)	0.0038 (4)	−0.0016 (4)
P1	0.01195 (16)	0.01266 (17)	0.01283 (16)	−0.00089 (13)	0.00241 (13)	0.00025 (13)
S1	0.01442 (16)	0.01179 (16)	0.01655 (16)	−0.00085 (12)	0.00194 (13)	0.00125 (13)
S2	0.01453 (16)	0.01163 (17)	0.01733 (16)	0.00058 (12)	0.00138 (13)	−0.00038 (13)
Ni1	0.01162 (12)	0.01061 (13)	0.01350 (12)	−0.00046 (9)	0.00235 (9)	0.00017 (9)

C1—C6	1.390 (2)	C8—H8A	0.9800
C1—C2	1.399 (2)	C8—H8B	0.9800
C1—P1	1.7871 (14)	C8—H8C	0.9800
C2—C3	1.384 (2)	C9—O2	1.4585 (17)
C2—H2	0.9500	C9—H9A	0.9800
C3—C4	1.398 (2)	C9—H9B	0.9800
C3—H3	0.9500	C9—H9C	0.9800
C4—O1	1.3606 (17)	O2—P1	1.5902 (10)
C4—C5	1.393 (2)	P1—S2	1.9996 (5)
C5—C6	1.391 (2)	P1—S1	2.0061 (5)
C5—H5	0.9500	P1—Ni1	2.8306 (4)
C6—H6	0.9500	S1—Ni1	2.2455 (3)
C7—O1	1.4408 (18)	S2—Ni1	2.2328 (4)
C7—C8	1.506 (2)	Ni1—S2i	2.2328 (4)
C7—H7A	0.9900	Ni1—S1i	2.2455 (3)
C7—H7B	0.9900	Ni1—P1i	2.8306 (4)
C6—C1—C2	119.07 (13)	O2—C9—H9C	109.5
C6—C1—P1	119.25 (11)	H9A—C9—H9C	109.5
C2—C1—P1	121.52 (11)	H9B—C9—H9C	109.5
C3—C2—C1	120.23 (14)	C4—O1—C7	118.63 (12)
C3—C2—H2	119.9	C9—O2—P1	118.47 (9)
C1—C2—H2	119.9	O2—P1—C1	101.76 (6)
C2—C3—C4	120.03 (14)	O2—P1—S2	113.60 (4)
C2—C3—H3	120.0	C1—P1—S2	113.88 (5)
C4—C3—H3	120.0	O2—P1—S1	113.49 (4)
O1—C4—C5	124.08 (14)	C1—P1—S1	112.10 (5)
O1—C4—C3	115.59 (13)	S2—P1—S1	102.47 (2)
C5—C4—C3	120.33 (13)	O2—P1—Ni1	138.74 (4)
C6—C5—C4	118.91 (14)	C1—P1—Ni1	119.49 (5)
C6—C5—H5	120.5	S2—P1—Ni1	51.639 (13)
C4—C5—H5	120.5	S1—P1—Ni1	51.985 (12)
C1—C6—C5	121.39 (14)	P1—S1—Ni1	83.279 (16)
C1—C6—H6	119.3	P1—S2—Ni1	83.755 (17)
C5—C6—H6	119.3	S2i—Ni1—S2	180.0
O1—C7—C8	106.33 (13)	S2i—Ni1—S1	91.557 (13)
O1—C7—H7A	110.5	S2—Ni1—S1	88.443 (13)
C8—C7—H7A	110.5	S2i—Ni1—S1i	88.443 (13)
O1—C7—H7B	110.5	S2—Ni1—S1i	91.557 (13)
C8—C7—H7B	110.5	S1—Ni1—S1i	180.0
H7A—C7—H7B	108.7	S2i—Ni1—P1i	44.606 (11)
C7—C8—H8A	109.5	S2—Ni1—P1i	135.394 (11)
C7—C8—H8B	109.5	S1—Ni1—P1i	135.263 (12)
H8A—C8—H8B	109.5	S1i—Ni1—P1i	44.737 (12)
C7—C8—H8C	109.5	S2i—Ni1—P1	135.394 (11)
H8A—C8—H8C	109.5	S2—Ni1—P1	44.606 (11)
H8B—C8—H8C	109.5	S1—Ni1—P1	44.737 (12)
O2—C9—H9A	109.5	S1i—Ni1—P1	135.263 (12)
O2—C9—H9B	109.5	P1i—Ni1—P1	180.0
H9A—C9—H9B	109.5
C6—C1—C2—C3	−0.8 (2)	C1—P1—S2—Ni1	−109.65 (5)
P1—C1—C2—C3	174.69 (12)	S1—P1—S2—Ni1	11.639 (18)
C1—C2—C3—C4	−0.5 (2)	P1—S2—Ni1—S2i	67 (100)
C2—C3—C4—O1	−178.75 (14)	P1—S2—Ni1—S1	−10.140 (16)
C2—C3—C4—C5	1.9 (2)	P1—S2—Ni1—S1i	169.860 (16)
O1—C4—C5—C6	178.78 (14)	P1—S2—Ni1—P1i	180.0
C3—C4—C5—C6	−1.9 (2)	P1—S1—Ni1—S2i	−169.884 (16)
C2—C1—C6—C5	0.7 (2)	P1—S1—Ni1—S2	10.116 (16)
P1—C1—C6—C5	−174.82 (13)	P1—S1—Ni1—S1i	−11 (100)
C4—C5—C6—C1	0.6 (2)	P1—S1—Ni1—P1i	180.0
C5—C4—O1—C7	1.5 (2)	O2—P1—Ni1—S2i	97.35 (7)
C3—C4—O1—C7	−177.89 (13)	C1—P1—Ni1—S2i	−81.64 (6)
C8—C7—O1—C4	178.93 (13)	S2—P1—Ni1—S2i	180.000 (1)
C9—O2—P1—C1	−177.47 (12)	S1—P1—Ni1—S2i	14.48 (2)
C9—O2—P1—S2	−54.64 (12)	O2—P1—Ni1—S2	−82.65 (7)
C9—O2—P1—S1	61.90 (12)	C1—P1—Ni1—S2	98.36 (6)
C9—O2—P1—Ni1	3.43 (15)	S1—P1—Ni1—S2	−165.52 (2)
C6—C1—P1—O2	−74.92 (13)	O2—P1—Ni1—S1	82.87 (7)
C2—C1—P1—O2	109.62 (12)	C1—P1—Ni1—S1	−96.12 (6)
C6—C1—P1—S2	162.44 (11)	S2—P1—Ni1—S1	165.52 (2)
C2—C1—P1—S2	−13.02 (14)	O2—P1—Ni1—S1i	−97.13 (7)
C6—C1—P1—S1	46.67 (13)	C1—P1—Ni1—S1i	83.88 (6)
C2—C1—P1—S1	−128.78 (11)	S2—P1—Ni1—S1i	−14.48 (2)
C6—C1—P1—Ni1	104.40 (12)	S1—P1—Ni1—S1i	180.0
C2—C1—P1—Ni1	−71.06 (13)	O2—P1—Ni1—P1i	−20 (100)
O2—P1—S1—Ni1	−134.48 (4)	C1—P1—Ni1—P1i	161 (100)
C1—P1—S1—Ni1	110.92 (5)	S2—P1—Ni1—P1i	63 (100)
S2—P1—S1—Ni1	−11.583 (18)	S1—P1—Ni1—P1i	−102 (100)
O2—P1—S2—Ni1	134.46 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ii	0.95	2.57	3.5123 (18)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.95	2.57	3.5123 (18)	171

Symmetry code: (i) .