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

The title compound, [Ni(C11H16O2PS2)2], contains a four-coordinate Ni(II) cation with an idealized square-planar geometry. The metal atom is surrounded by two chelating isobidentate dithio-phospho-nate ligands in a trans or anti configuration, binding through the S-donor atoms.

Related literature

For information on the first structure of an NiII–dithiophosphonate complex, see: Hartung (1967 ▶). For general preparative procedures for dithiophosphonates, see: Van Zyl (2010 ▶); Van Zyl & Fackler (2000 ▶). For a comprehensive review on dithiophosphonates, see: Van Zyl & Woollins (2012 ▶). For reports on the synthesis and structures of different types of NiII–dithiophosphonate complexes, see: Liu et al. (2004 ▶); Gray et al. (2004 ▶); Aragoni et al. (2007 ▶); Arca et al. (1997 ▶).

Experimental

Crystal data

[Ni(C11H16O2PS2)2]

M = 609.37

Monoclinic,

a = 9.4227 (2) Å

b = 15.6479 (3) Å

c = 9.5281 (2) Å

β = 102.878 (1)°

V = 1369.54 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.16 mm−1

T = 173 K

0.40 × 0.34 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.655, T max = 0.883

32798 measured reflections

3446 independent reflections

3335 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.053

S = 1.09

3446 reflections

153 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.39 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/S1600536812047368/fj2606sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047368/fj2606Isup2.hkl

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

[Ni(C11H16O2PS2)2]	F(000) = 636
Mr = 609.37	Dx = 1.478 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 32798 reflections
a = 9.4227 (2) Å	θ = 2.2–28.8°
b = 15.6479 (3) Å	µ = 1.16 mm−1
c = 9.5281 (2) Å	T = 173 K
β = 102.878 (1)°	Block, purple
V = 1369.54 (5) Å3	0.40 × 0.34 × 0.11 mm
Z = 2

Bruker APEXII CCD diffractometer	3446 independent reflections
Radiation source: fine-focus sealed tube	3335 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 28.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.655, Tmax = 0.883	k = −20→20
32798 measured reflections	l = −12→12

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.053	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0288P)2 + 0.5042P] where P = (Fo2 + 2Fc2)/3
3446 reflections	(Δ/σ)max = 0.001
153 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.39 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	0.29971 (11)	−0.07749 (6)	0.10196 (10)	0.01471 (18)
C2	0.31929 (11)	−0.15981 (7)	0.15941 (11)	0.01713 (19)
H2	0.3857	−0.1688	0.2490	0.021*
C3	0.24319 (11)	−0.22889 (7)	0.08761 (11)	0.01787 (19)
H3	0.2576	−0.2847	0.1275	0.021*
C4	0.14523 (11)	−0.21525 (7)	−0.04391 (11)	0.01670 (19)
C5	0.12225 (11)	−0.13257 (7)	−0.10066 (11)	0.0193 (2)
H5	0.0537	−0.1233	−0.1889	0.023*
C6	0.19899 (11)	−0.06433 (7)	−0.02877 (11)	0.01805 (19)
H6	0.1835	−0.0084	−0.0680	0.022*
C7	0.08205 (13)	−0.36349 (7)	−0.07133 (13)	0.0237 (2)
H7A	0.0514	−0.3672	0.0214	0.028*
H7B	0.1845	−0.3826	−0.0560	0.028*
C8	−0.01499 (13)	−0.41831 (8)	−0.18383 (15)	0.0293 (3)
H8A	−0.1153	−0.3973	−0.2004	0.044*
H8B	−0.0113	−0.4776	−0.1501	0.044*
H8C	0.0187	−0.4156	−0.2739	0.044*
C9	0.45560 (11)	0.16125 (6)	0.09836 (11)	0.01833 (19)
H9A	0.5607	0.1608	0.0983	0.022*
H9B	0.4439	0.1817	0.1935	0.022*
C10	0.37431 (12)	0.21896 (7)	−0.01933 (13)	0.0217 (2)
H10A	0.3759	0.1934	−0.1140	0.026*
H10B	0.4247	0.2748	−0.0132	0.026*
C11	0.21705 (14)	0.23324 (9)	−0.00963 (17)	0.0339 (3)
H11A	0.1684	0.1779	−0.0093	0.051*
H11B	0.1666	0.2668	−0.0927	0.051*
H11C	0.2149	0.2642	0.0793	0.051*
O1	0.06717 (8)	−0.27749 (5)	−0.12533 (8)	0.02031 (15)
O2	0.39444 (8)	0.07533 (5)	0.06998 (8)	0.01738 (15)
P1	0.39744 (3)	0.010268 (16)	0.19771 (3)	0.01352 (6)
S2	0.30614 (3)	0.057093 (16)	0.35296 (3)	0.01596 (6)
S4	0.40325 (3)	0.020730 (18)	0.69008 (3)	0.01702 (6)
Ni1	0.5000	0.0000	0.5000	0.01246 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0179 (4)	0.0127 (4)	0.0136 (4)	−0.0006 (3)	0.0037 (3)	−0.0009 (3)
C2	0.0203 (4)	0.0160 (5)	0.0145 (4)	0.0006 (4)	0.0025 (3)	0.0016 (4)
C3	0.0214 (5)	0.0135 (4)	0.0188 (5)	−0.0003 (4)	0.0049 (4)	0.0014 (4)
C4	0.0166 (4)	0.0159 (5)	0.0185 (4)	−0.0024 (4)	0.0058 (4)	−0.0034 (4)
C5	0.0198 (5)	0.0195 (5)	0.0167 (5)	−0.0009 (4)	−0.0003 (4)	0.0002 (4)
C6	0.0218 (5)	0.0142 (4)	0.0169 (5)	0.0003 (4)	0.0016 (4)	0.0017 (3)
C7	0.0246 (5)	0.0148 (5)	0.0315 (6)	−0.0027 (4)	0.0060 (4)	−0.0044 (4)
C8	0.0228 (5)	0.0204 (5)	0.0436 (7)	−0.0046 (4)	0.0050 (5)	−0.0106 (5)
C9	0.0231 (5)	0.0132 (4)	0.0191 (5)	−0.0042 (4)	0.0054 (4)	−0.0005 (4)
C10	0.0220 (5)	0.0158 (5)	0.0283 (5)	0.0011 (4)	0.0079 (4)	0.0049 (4)
C11	0.0239 (6)	0.0256 (6)	0.0537 (8)	0.0051 (5)	0.0119 (5)	0.0057 (6)
O1	0.0216 (4)	0.0159 (3)	0.0225 (4)	−0.0040 (3)	0.0029 (3)	−0.0041 (3)
O2	0.0258 (4)	0.0121 (3)	0.0136 (3)	−0.0032 (3)	0.0030 (3)	0.0007 (3)
P1	0.01689 (12)	0.01224 (12)	0.01123 (12)	−0.00026 (8)	0.00272 (9)	0.00008 (8)
S2	0.01740 (12)	0.01656 (12)	0.01382 (11)	0.00237 (8)	0.00325 (9)	−0.00129 (8)
S4	0.01565 (11)	0.02265 (13)	0.01304 (12)	0.00131 (9)	0.00382 (9)	−0.00118 (9)
Ni1	0.01398 (9)	0.01286 (9)	0.01053 (9)	−0.00043 (6)	0.00272 (7)	−0.00086 (6)

C1—C2	1.3957 (14)	C9—C10	1.5089 (14)
C1—C6	1.4028 (13)	C9—H9A	0.9900
C1—P1	1.7865 (10)	C9—H9B	0.9900
C2—C3	1.3899 (14)	C10—C11	1.5216 (16)
C2—H2	0.9500	C10—H10A	0.9900
C3—C4	1.3973 (14)	C10—H10B	0.9900
C3—H3	0.9500	C11—H11A	0.9800
C4—O1	1.3554 (12)	C11—H11B	0.9800
C4—C5	1.4004 (14)	C11—H11C	0.9800
C5—C6	1.3825 (14)	O2—P1	1.5822 (7)
C5—H5	0.9500	P1—S4i	2.0026 (4)
C6—H6	0.9500	P1—S2	2.0081 (3)
C7—O1	1.4364 (13)	P1—Ni1	2.8310 (3)
C7—C8	1.5113 (16)	S2—Ni1	2.2264 (2)
C7—H7A	0.9900	S4—P1i	2.0026 (4)
C7—H7B	0.9900	S4—Ni1	2.2254 (2)
C8—H8A	0.9800	Ni1—S4i	2.2254 (2)
C8—H8B	0.9800	Ni1—S2i	2.2264 (2)
C8—H8C	0.9800	Ni1—P1i	2.8310 (3)
C9—O2	1.4640 (12)
C2—C1—C6	119.20 (9)	C9—C10—H10B	109.1
C2—C1—P1	120.07 (7)	C11—C10—H10B	109.1
C6—C1—P1	120.69 (8)	H10A—C10—H10B	107.8
C3—C2—C1	121.07 (9)	C10—C11—H11A	109.5
C3—C2—H2	119.5	C10—C11—H11B	109.5
C1—C2—H2	119.5	H11A—C11—H11B	109.5
C2—C3—C4	119.20 (9)	C10—C11—H11C	109.5
C2—C3—H3	120.4	H11A—C11—H11C	109.5
C4—C3—H3	120.4	H11B—C11—H11C	109.5
O1—C4—C3	124.71 (9)	C4—O1—C7	118.10 (8)
O1—C4—C5	115.18 (9)	C9—O2—P1	120.67 (6)
C3—C4—C5	120.12 (9)	O2—P1—C1	100.55 (4)
C6—C5—C4	120.23 (9)	O2—P1—S4i	114.86 (3)
C6—C5—H5	119.9	C1—P1—S4i	113.69 (3)
C4—C5—H5	119.9	O2—P1—S2	113.25 (3)
C5—C6—C1	120.15 (9)	C1—P1—S2	113.57 (3)
C5—C6—H6	119.9	S4i—P1—S2	101.530 (15)
C1—C6—H6	119.9	O2—P1—Ni1	139.70 (3)
O1—C7—C8	106.40 (10)	C1—P1—Ni1	119.74 (3)
O1—C7—H7A	110.4	S4i—P1—Ni1	51.409 (9)
C8—C7—H7A	110.4	S2—P1—Ni1	51.421 (9)
O1—C7—H7B	110.4	P1—S2—Ni1	83.742 (11)
C8—C7—H7B	110.4	P1i—S4—Ni1	83.894 (11)
H7A—C7—H7B	108.6	S4i—Ni1—S4	180.0
C7—C8—H8A	109.5	S4i—Ni1—S2i	91.498 (9)
C7—C8—H8B	109.5	S4—Ni1—S2i	88.502 (9)
H8A—C8—H8B	109.5	S4i—Ni1—S2	88.502 (9)
C7—C8—H8C	109.5	S4—Ni1—S2	91.498 (9)
H8A—C8—H8C	109.5	S2i—Ni1—S2	180.0
H8B—C8—H8C	109.5	S4i—Ni1—P1i	135.304 (8)
O2—C9—C10	107.37 (8)	S4—Ni1—P1i	44.696 (8)
O2—C9—H9A	110.2	S2i—Ni1—P1i	44.837 (8)
C10—C9—H9A	110.2	S2—Ni1—P1i	135.163 (8)
O2—C9—H9B	110.2	S4i—Ni1—P1	44.696 (8)
C10—C9—H9B	110.2	S4—Ni1—P1	135.304 (8)
H9A—C9—H9B	108.5	S2i—Ni1—P1	135.163 (8)
C9—C10—C11	112.50 (10)	S2—Ni1—P1	44.837 (8)
C9—C10—H10A	109.1	P1i—Ni1—P1	180.0
C11—C10—H10A	109.1
C6—C1—C2—C3	1.47 (15)	C6—C1—P1—Ni1	153.56 (7)
C1—C2—C3—C4	−0.24 (15)	O2—P1—S2—Ni1	−135.98 (3)
C2—C3—C4—C5	−1.32 (15)	C1—P1—S2—Ni1	110.14 (4)
C3—C4—C5—C6	1.64 (16)	S4i—P1—S2—Ni1	−12.297 (14)
C4—C5—C6—C1	−0.40 (16)	P1i—S4—Ni1—S2i	10.854 (12)
C2—C1—C6—C5	−1.14 (15)	P1i—S4—Ni1—S2	−169.146 (12)
O2—C9—C10—C11	68.95 (12)	P1—S2—Ni1—S4i	10.827 (12)
C3—C4—O1—C7	2.04 (15)	P1—S2—Ni1—S4	−169.173 (12)
C10—C9—O2—P1	−151.82 (7)	O2—P1—Ni1—S4i	−83.72 (5)
C9—O2—P1—C1	176.20 (7)	C1—P1—Ni1—S4i	97.82 (4)
C9—O2—P1—S4i	−61.34 (8)	S2—P1—Ni1—S4i	−164.515 (17)
C9—O2—P1—S2	54.69 (8)	O2—P1—Ni1—S4	96.28 (5)
C9—O2—P1—Ni1	−2.44 (10)	C1—P1—Ni1—S4	−82.18 (4)
C2—C1—P1—O2	156.81 (8)	S2—P1—Ni1—S4	15.485 (17)
C6—C1—P1—O2	−25.43 (9)	O2—P1—Ni1—S2i	−99.21 (5)
C2—C1—P1—S4i	33.54 (9)	C1—P1—Ni1—S2i	82.33 (4)
C6—C1—P1—S4i	−148.71 (7)	S4i—P1—Ni1—S2i	−15.485 (17)
C2—C1—P1—S2	−81.91 (8)	O2—P1—Ni1—S2	80.79 (5)
C6—C1—P1—S2	95.85 (8)	C1—P1—Ni1—S2	−97.67 (4)
C2—C1—P1—Ni1	−24.20 (10)	S4i—P1—Ni1—S2	164.515 (17)