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

The title compound, [Ni(C11H16O2PS2)2], is a neutral four-coordinate mononuclear complex with a square-planar geometry. The complex lies on an inversion center. The metal atom is surrounded by two chelating isobidentate O-propan-2-yl (4-eth-oxy-phen-yl)dithio-phospho-nate ligands in a trans configuration binding through the S-donor atoms. The Ni-S bond lengths are 2.2328 (5) and 2.2369 (5) Å, an insignificant difference to be considered anisobidentate. The Ni⋯P separation is 2.8224 (5) Å and the S-P bond lengths are 2.0035 (7) and 2.0053 (7) Å. The S-Ni-S (chelating) and S-Ni-S (trans) bond angles are 88.321 (18) and 180°. The Ni-S-P bond angles are 83.26 (2) and 83.33 (2)°, indicating a very minor distortion from ideal square-planar geometry for the Ni atom. The P atom, however, is distorted quite significantly from an ideal tetra-hedral geometry, as reflected by the S-P-S and O-P-C bond angles of 101.93 (3) and 100.70 (7)°, respectively.

Related literature

For information on dithio­phospho­nate compounds, see: Van Zyl & Fackler (2000 ▶); Van Zyl (2010 ▶). For examples of nickel(II) dithio­phospho­nate complexes, see: Liu et al. (2004 ▶); Gray et al. (2004 ▶); Aragoni et al. (2007 ▶); Arca et al. (1997 ▶); Malatesta & Pizzotti (1945 ▶); Hartung (1967 ▶).

Experimental

Crystal data

[Ni(C11H16O2PS2)2]

M = 609.37

Triclinic,

a = 7.8893 (6) Å

b = 8.4178 (7) Å

c = 11.4825 (10) Å

α = 109.530 (4)°

β = 101.959 (4)°

γ = 93.913 (5)°

V = 695.22 (10) Å3

Z = 1

Mo Kα radiation

μ = 1.14 mm−1

T = 173 K

0.39 × 0.26 × 0.14 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.665, T max = 0.857

14410 measured reflections

3062 independent reflections

2381 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.065

S = 1.02

3062 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.31 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; 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/S1600536812045114/bh2460sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045114/bh2460Isup2.hkl

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

[Ni(C11H16O2PS2)2]	Z = 1
Mr = 609.37	F(000) = 318
Triclinic, P1	Dx = 1.455 Mg m−3
Hall symbol: -P 1	Melting point: 441 K
a = 7.8893 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4178 (7) Å	Cell parameters from 14410 reflections
c = 11.4825 (10) Å	θ = 2.6–27.5°
α = 109.530 (4)°	µ = 1.14 mm−1
β = 101.959 (4)°	T = 173 K
γ = 93.913 (5)°	Block, purple
V = 695.22 (10) Å3	0.39 × 0.26 × 0.14 mm

Nonius KappaCCD diffractometer	3062 independent reflections
Radiation source: fine-focus sealed tube	2381 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
1.2° φ scans and ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = 0→10
Tmin = 0.665, Tmax = 0.857	k = −10→10
14410 measured reflections	l = −14→14

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.028P)2 + 0.2462P] where P = (Fo2 + 2Fc2)/3
3062 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.31 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.5000	0.0000	0.02229 (10)
S1	0.64099 (6)	0.75272 (6)	0.02356 (5)	0.02729 (13)
S2	0.58144 (7)	0.38847 (6)	−0.18193 (5)	0.02842 (13)
P1	0.64598 (6)	0.63370 (6)	−0.15849 (5)	0.02271 (12)
O1	0.19743 (19)	0.8621 (2)	−0.53641 (14)	0.0416 (4)
O2	0.82744 (15)	0.67472 (17)	−0.18857 (12)	0.0266 (3)
C1	0.5013 (2)	0.7025 (2)	−0.26799 (17)	0.0231 (4)
C2	0.4982 (3)	0.8752 (3)	−0.2422 (2)	0.0317 (5)
H2	0.5664	0.9551	−0.1634	0.038*
C3	0.3977 (3)	0.9335 (3)	−0.3289 (2)	0.0336 (5)
H3	0.3976	1.0523	−0.3099	0.040*
C4	0.2974 (2)	0.8179 (3)	−0.44330 (19)	0.0308 (5)
C5	0.2947 (3)	0.6447 (3)	−0.4682 (2)	0.0405 (6)
H5	0.2227	0.5647	−0.5455	0.049*
C6	0.3960 (3)	0.5880 (3)	−0.3815 (2)	0.0360 (5)
H6	0.3937	0.4690	−0.3996	0.043*
C7	0.2176 (3)	1.0381 (3)	−0.5253 (2)	0.0463 (6)
H7A	0.3430	1.0834	−0.5079	0.056*
H7B	0.1696	1.1073	−0.4548	0.056*
C8	0.1178 (3)	1.0441 (4)	−0.6510 (3)	0.0654 (8)
H8A	0.1653	0.9734	−0.7200	0.098*
H8B	0.1299	1.1621	−0.6482	0.098*
H8C	−0.0063	1.0008	−0.6662	0.098*
C9	0.9927 (2)	0.6387 (3)	−0.11992 (19)	0.0302 (5)
H9	0.9693	0.6009	−0.0502	0.036*
C10	1.1185 (3)	0.8017 (3)	−0.0629 (3)	0.0646 (8)
H10A	1.1334	0.8447	−0.1302	0.097*
H10B	1.2319	0.7811	−0.0211	0.097*
H10C	1.0725	0.8863	0.0001	0.097*
C11	1.0541 (3)	0.4983 (3)	−0.2128 (2)	0.0567 (7)
H11A	0.9642	0.3971	−0.2481	0.085*
H11B	1.1628	0.4711	−0.1695	0.085*
H11C	1.0758	0.5343	−0.2819	0.085*

	U11	U22	U33	U12	U13	U23
Ni1	0.02098 (18)	0.0252 (2)	0.0246 (2)	0.00292 (14)	0.00633 (14)	0.01367 (16)
S1	0.0299 (3)	0.0276 (3)	0.0257 (3)	0.0000 (2)	0.0069 (2)	0.0119 (2)
S2	0.0343 (3)	0.0258 (3)	0.0305 (3)	0.0050 (2)	0.0128 (2)	0.0138 (2)
P1	0.0197 (2)	0.0268 (3)	0.0260 (3)	0.00378 (19)	0.0065 (2)	0.0145 (2)
O1	0.0440 (9)	0.0502 (10)	0.0364 (9)	0.0170 (7)	0.0024 (7)	0.0253 (8)
O2	0.0170 (6)	0.0397 (8)	0.0333 (8)	0.0077 (6)	0.0074 (6)	0.0248 (7)
C1	0.0184 (9)	0.0282 (11)	0.0257 (10)	0.0047 (8)	0.0065 (8)	0.0125 (9)
C2	0.0288 (11)	0.0299 (12)	0.0315 (12)	0.0026 (9)	−0.0009 (9)	0.0100 (10)
C3	0.0329 (11)	0.0284 (11)	0.0413 (13)	0.0073 (9)	0.0041 (10)	0.0170 (10)
C4	0.0259 (10)	0.0406 (13)	0.0323 (12)	0.0111 (9)	0.0076 (9)	0.0198 (10)
C5	0.0466 (14)	0.0352 (13)	0.0292 (12)	0.0069 (10)	−0.0062 (10)	0.0073 (10)
C6	0.0407 (12)	0.0283 (11)	0.0355 (12)	0.0090 (9)	0.0008 (10)	0.0112 (10)
C7	0.0392 (13)	0.0601 (16)	0.0630 (16)	0.0159 (11)	0.0154 (12)	0.0483 (14)
C8	0.0461 (15)	0.107 (2)	0.082 (2)	0.0262 (15)	0.0198 (14)	0.0779 (19)
C9	0.0194 (10)	0.0415 (12)	0.0363 (12)	0.0080 (9)	0.0029 (8)	0.0240 (10)
C10	0.0313 (13)	0.0465 (15)	0.097 (2)	0.0041 (11)	−0.0166 (14)	0.0217 (16)
C11	0.0352 (13)	0.0701 (18)	0.0548 (17)	0.0292 (12)	−0.0002 (12)	0.0123 (14)

Ni1—S2	2.2328 (5)	C4—C5	1.387 (3)
Ni1—S2i	2.2328 (5)	C5—C6	1.378 (3)
Ni1—S1i	2.2369 (5)	C5—H5	0.9500
Ni1—S1	2.2369 (5)	C6—H6	0.9500
Ni1—P1	2.8224 (5)	C7—C8	1.513 (3)
Ni1—P1i	2.8224 (5)	C7—H7A	0.9900
S1—P1	2.0035 (7)	C7—H7B	0.9900
S2—P1	2.0053 (7)	C8—H8A	0.9800
P1—O2	1.5828 (12)	C8—H8B	0.9800
P1—C1	1.7894 (18)	C8—H8C	0.9800
O1—C4	1.364 (2)	C9—C11	1.489 (3)
O1—C7	1.438 (3)	C9—C10	1.497 (3)
O2—C9	1.484 (2)	C9—H9	1.0000
C1—C6	1.385 (3)	C10—H10A	0.9800
C1—C2	1.386 (3)	C10—H10B	0.9800
C2—C3	1.383 (3)	C10—H10C	0.9800
C2—H2	0.9500	C11—H11A	0.9800
C3—C4	1.381 (3)	C11—H11B	0.9800
C3—H3	0.9500	C11—H11C	0.9800
S2—Ni1—S2i	180.0	O1—C4—C5	116.20 (19)
S2—Ni1—S1i	91.679 (18)	C3—C4—C5	119.59 (18)
S2i—Ni1—S1i	88.321 (18)	C6—C5—C4	120.3 (2)
S2—Ni1—S1	88.321 (18)	C6—C5—H5	119.8
S2i—Ni1—S1	91.679 (18)	C4—C5—H5	119.8
S1i—Ni1—S1	180.0	C5—C6—C1	120.7 (2)
S2—Ni1—P1	44.885 (16)	C5—C6—H6	119.6
S2i—Ni1—P1	135.115 (17)	C1—C6—H6	119.6
S1i—Ni1—P1	135.174 (16)	O1—C7—C8	106.7 (2)
S1—Ni1—P1	44.827 (16)	O1—C7—H7A	110.4
S2—Ni1—P1i	135.115 (16)	C8—C7—H7A	110.4
S2i—Ni1—P1i	44.885 (16)	O1—C7—H7B	110.4
S1i—Ni1—P1i	44.827 (16)	C8—C7—H7B	110.4
S1—Ni1—P1i	135.173 (16)	H7A—C7—H7B	108.6
P1—Ni1—P1i	180.0	C7—C8—H8A	109.5
P1—S1—Ni1	83.26 (2)	C7—C8—H8B	109.5
P1—S2—Ni1	83.33 (2)	H8A—C8—H8B	109.5
O2—P1—C1	100.70 (7)	C7—C8—H8C	109.5
O2—P1—S1	113.76 (6)	H8A—C8—H8C	109.5
C1—P1—S1	113.38 (7)	H8B—C8—H8C	109.5
O2—P1—S2	114.16 (6)	O2—C9—C11	107.84 (16)
C1—P1—S2	113.47 (7)	O2—C9—C10	107.22 (17)
S1—P1—S2	101.93 (3)	C11—C9—C10	113.9 (2)
O2—P1—Ni1	141.40 (5)	O2—C9—H9	109.3
C1—P1—Ni1	117.90 (6)	C11—C9—H9	109.3
S1—P1—Ni1	51.913 (17)	C10—C9—H9	109.3
S2—P1—Ni1	51.790 (18)	C9—C10—H10A	109.5
C4—O1—C7	118.46 (17)	C9—C10—H10B	109.5
C9—O2—P1	121.36 (11)	H10A—C10—H10B	109.5
C6—C1—C2	118.40 (18)	C9—C10—H10C	109.5
C6—C1—P1	121.83 (15)	H10A—C10—H10C	109.5
C2—C1—P1	119.72 (15)	H10B—C10—H10C	109.5
C3—C2—C1	121.31 (19)	C9—C11—H11A	109.5
C3—C2—H2	119.3	C9—C11—H11B	109.5
C1—C2—H2	119.3	H11A—C11—H11B	109.5
C4—C3—C2	119.60 (19)	C9—C11—H11C	109.5
C4—C3—H3	120.2	H11A—C11—H11C	109.5
C2—C3—H3	120.2	H11B—C11—H11C	109.5
O1—C4—C3	124.21 (19)
S2—Ni1—S1—P1	12.58 (2)	S1—P1—O2—C9	58.46 (15)
S2i—Ni1—S1—P1	−167.42 (2)	S2—P1—O2—C9	−57.97 (15)
P1i—Ni1—S1—P1	180.0	Ni1—P1—O2—C9	0.38 (19)
S1i—Ni1—S2—P1	167.43 (2)	O2—P1—C1—C6	101.89 (17)
S1—Ni1—S2—P1	−12.57 (2)	S1—P1—C1—C6	−136.21 (15)
P1i—Ni1—S2—P1	180.0	S2—P1—C1—C6	−20.53 (18)
Ni1—S1—P1—O2	−137.71 (6)	Ni1—P1—C1—C6	−78.31 (17)
Ni1—S1—P1—C1	107.99 (7)	O2—P1—C1—C2	−75.50 (16)
Ni1—S1—P1—S2	−14.35 (3)	S1—P1—C1—C2	46.41 (17)
Ni1—S2—P1—O2	137.47 (6)	S2—P1—C1—C2	162.08 (14)
Ni1—S2—P1—C1	−107.90 (7)	Ni1—P1—C1—C2	104.30 (15)
Ni1—S2—P1—S1	14.37 (3)	C6—C1—C2—C3	−2.3 (3)
S2—Ni1—P1—O2	−81.30 (9)	P1—C1—C2—C3	175.20 (15)
S2i—Ni1—P1—O2	98.70 (9)	C1—C2—C3—C4	0.4 (3)
S1i—Ni1—P1—O2	−99.27 (9)	C7—O1—C4—C3	10.4 (3)
S1—Ni1—P1—O2	80.73 (9)	C7—O1—C4—C5	−169.75 (19)
S2—Ni1—P1—C1	99.02 (8)	C2—C3—C4—O1	−178.27 (18)
S2i—Ni1—P1—C1	−80.98 (8)	C2—C3—C4—C5	1.9 (3)
S1i—Ni1—P1—C1	81.05 (8)	O1—C4—C5—C6	177.9 (2)
S1—Ni1—P1—C1	−98.95 (8)	C3—C4—C5—C6	−2.2 (3)
S2—Ni1—P1—S1	−162.03 (3)	C4—C5—C6—C1	0.3 (3)
S2i—Ni1—P1—S1	17.97 (3)	C2—C1—C6—C5	1.9 (3)
S1i—Ni1—P1—S1	180.000 (1)	P1—C1—C6—C5	−175.49 (17)
S2i—Ni1—P1—S2	180.0	C4—O1—C7—C8	169.83 (18)
S1i—Ni1—P1—S2	−17.97 (3)	P1—O2—C9—C11	112.06 (18)
S1—Ni1—P1—S2	162.03 (3)	P1—O2—C9—C10	−124.87 (18)
C1—P1—O2—C9	−179.91 (14)