(meso-5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetra­azacyclo­tetra­deca-4,11-diene)nickel(II) bis­[O,O′-bis(4-methyl­phen­yl) dithio­phosphate]

Xie, B.; Xiang, Y.-G.; Zou, L.-K.; Chang, X.-L.; Ji, C.-Y.

doi:10.1107/S1600536809030955

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1053

doi:10.1107/S1600536809030955

Open

access

(meso-5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetraazacyclotetradeca-4,11-diene)nickel(II) bis[O,O′-bis(4-methylphenyl) dithiophosphate]

Bin Xie,^a ^* Yang-Guang Xiang,^a Li-Ke Zou,^a Xiu-Li Chang ^a and Chang-You Ji ^b

^aCollege of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, 643000 Zigong, Sichuan, People's Republic of China, and ^bCollege of Environment and Chemical Engineering, Xi'an Polytechnic University, 710048 Xi'an, Shanxi, People's Republic of China
^*Correspondence e-mail: zoulike@yahoo.com.cn

(Received 22 July 2009; accepted 4 August 2009; online 8 August 2009)

In the title compound, [Ni(C₁₆H₃₂N₄)](C₁₄H₁₄O₂PS₂)₂ or [Ni(trans[14]dien)][S₂P(OC₆H₄Me-4)₂]₂, where trans[14]dien is meso-5,7,7,12,14,14-hexamethyl-1,4,8,11-tetraazacyclotetradeca-4,11-diene, the Ni^II ion lies across a centre of inversion and is four-coordinated in a relatively undistorted square-planar arrangement by the four N atoms of the macrocyclic ligand trans[14]dien. The two O,O′-di(4-methylphenyl)dithiophosphates act as counter-ions to balance the charge. Important geometric data include Ni—N = 1.9135 (16) and 1.9364 (15) Å.

Related literature

For related structures, see: Xie et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Ni(C₁₆H₃₂N₄)](C₁₄H₁₄O₂PS₂)₂
M_r = 957.85
Triclinic, $[P \overline 1]$
a = 8.0044 (6) Å
b = 10.0996 (8) Å
c = 16.4004 (12) Å
α = 80.418 (1)°
β = 81.333 (1)°
γ = 69.836 (1)°
V = 1220.95 (16) Å³
Z = 1
Mo Kα radiation
μ = 0.68 mm⁻¹
T = 278 K
0.18 × 0.14 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.888, T_max = 0.935
6525 measured reflections
4305 independent reflections
3756 reflections with I > 2σ(I)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.04
4305 reflections
273 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030955/dn2479sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030955/dn2479Isup2.hkl

checkCIF report

Comment top

As part of an investigation to the potential applications of tetramine macrocyclic transition metal complexs as artificial enzyme models, we have recently reported the structures of [Ni(teta)][S₂P(OCH₂Ph)₂]₂, where teta is meso-5,5,7,12,12,14- hexamethyl-1,4,8,11-tetraazacyclotetradecane (Xie et al., 2008). Here we report the structure of [Ni(trans[14]dien)] [S₂P(OC₆H₄Me-4)₂]₂, where trans[14]dien is meso-5,7,7,12,14,14- hexamethyl-1,4,8,11-tetraazacyclotetradeca-4,11-diene.

In the title compound, the Ni^II atom exhibits a relatively undistorted square-planar geometry (Fig.1), which lies on an inversion centre and is coordinated by four N atoms of the macrocyclic ligand trans[14]dien. The two O,O'-di(4-methylphenyl) dithiophosphates only act as counter-ions to balance the charge.All the bond lengths and angles in the complex are generally within normal ranges (Allen et al., 1987).

Related literature top

For related structures, see: Xie et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

meso-5,7,7,12,14,14-Hexamethyl-1,4,8,1 l-tetraazacyclotetradeca-4, 11-diene nickel(II) perchlorate(2 mmol 1.28 g) was added to a solution of diethylammonium O,O'-di(4-methylphenyl)dithiophosphate (4 mmol 1.534 g) in 60 ml methanol. The mixture was refluxed for 8 h at 353 K and then filtered. The filtrate was kept at room temperature and orange block crystals were obtained after 4 days.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.H atoms have been omitted for the sake of clarity.[Symmetry code: (i) -x + 1, -y + 1, -z + 1].

(meso-5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetraazacyclotetradeca-4,11- diene)nickel(II) bis[O,O'-bis(4-methylphenyl) dithiophosphate] top

Crystal data top

[Ni(C₁₆H₃₂N₄)](C₁₄H₁₄O₂PS₂)₂	Z = 1
M_r = 957.85	F(000) = 506
Triclinic, P1	D_x = 1.303 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0044 (6) Å	Cell parameters from 3628 reflections
b = 10.0996 (8) Å	θ = 2.4–28.3°
c = 16.4004 (12) Å	µ = 0.68 mm⁻¹
α = 80.418 (1)°	T = 278 K
β = 81.333 (1)°	Block, orange
γ = 69.836 (1)°	0.18 × 0.14 × 0.10 mm
V = 1220.95 (16) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4305 independent reflections
Radiation source: fine-focus sealed tube	3756 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→6
T_min = 0.888, T_max = 0.935	k = −12→11
6525 measured reflections	l = −18→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0404P)² + 0.4007P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4305 reflections	Δρ_max = 0.50 e Å⁻³
273 parameters	Δρ_min = −0.34 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0094 (11)

Crystal data top

[Ni(C₁₆H₃₂N₄)](C₁₄H₁₄O₂PS₂)₂	γ = 69.836 (1)°
M_r = 957.85	V = 1220.95 (16) Å³
Triclinic, P1	Z = 1
a = 8.0044 (6) Å	Mo Kα radiation
b = 10.0996 (8) Å	µ = 0.68 mm⁻¹
c = 16.4004 (12) Å	T = 278 K
α = 80.418 (1)°	0.18 × 0.14 × 0.10 mm
β = 81.333 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4305 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3756 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.935	R_int = 0.012
6525 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.50 e Å⁻³
4305 reflections	Δρ_min = −0.34 e Å⁻³
273 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	0.5000	0.5000	0.5000	0.03886 (12)
S1	0.51679 (8)	0.93375 (7)	0.29986 (4)	0.06565 (19)
S2	0.80706 (8)	0.63426 (7)	0.38281 (4)	0.06475 (18)
P1	0.74959 (7)	0.78569 (6)	0.28970 (4)	0.05003 (16)
O1	0.9135 (2)	0.84827 (17)	0.27241 (10)	0.0615 (4)
O2	0.7837 (2)	0.72019 (16)	0.20251 (9)	0.0582 (4)
N1	0.3850 (2)	0.48109 (17)	0.41047 (10)	0.0448 (4)
N2	0.3765 (2)	0.70211 (16)	0.47728 (11)	0.0437 (4)
C1	0.3764 (3)	0.3675 (2)	0.38841 (13)	0.0507 (5)
C2	0.2623 (4)	0.3675 (3)	0.32375 (19)	0.0806 (8)
H2A	0.1387	0.4131	0.3418	0.121*
H2B	0.2803	0.2713	0.3157	0.121*
H2C	0.2948	0.4180	0.2723	0.121*
C3	0.4795 (3)	0.2249 (2)	0.42779 (15)	0.0581 (6)
H3A	0.4977	0.1572	0.3891	0.070*
H3B	0.4060	0.1994	0.4763	0.070*
C4	0.2860 (3)	0.6213 (2)	0.36823 (15)	0.0578 (6)
H4A	0.1864	0.6155	0.3436	0.069*
H4B	0.3640	0.6542	0.3247	0.069*
C5	0.2199 (3)	0.7204 (2)	0.43308 (16)	0.0586 (6)
H5A	0.1723	0.8178	0.4076	0.070*
H5B	0.1264	0.6972	0.4714	0.070*
C6	0.3396 (3)	0.7936 (2)	0.54526 (14)	0.0509 (5)
C7	0.2575 (4)	0.9514 (2)	0.51212 (18)	0.0716 (7)
H7A	0.3355	0.9768	0.4665	0.107*
H7B	0.2426	1.0087	0.5556	0.107*
H7C	0.1432	0.9671	0.4936	0.107*
C8	0.2158 (3)	0.7501 (2)	0.61610 (16)	0.0668 (6)
H8A	0.0998	0.7719	0.5978	0.100*
H8B	0.2055	0.8010	0.6621	0.100*
H8C	0.2639	0.6498	0.6332	0.100*
C9	0.9401 (3)	0.9521 (2)	0.20917 (14)	0.0520 (5)
C10	1.0778 (3)	0.9987 (3)	0.21639 (16)	0.0643 (6)
H10	1.1433	0.9634	0.2621	0.077*
C11	1.1198 (4)	1.0978 (3)	0.15607 (17)	0.0743 (7)
H11	1.2137	1.1288	0.1618	0.089*
C12	1.0265 (4)	1.1519 (3)	0.08774 (16)	0.0706 (7)
C13	0.8887 (4)	1.1040 (3)	0.08206 (17)	0.0816 (8)
H13	0.8233	1.1392	0.0363	0.098*
C14	0.8432 (4)	1.0046 (3)	0.14216 (17)	0.0733 (7)
H14	0.7485	0.9742	0.1370	0.088*
C15	1.0710 (5)	1.2625 (4)	0.0212 (2)	0.1070 (11)
H15A	1.0213	1.2641	−0.0288	0.161*
H15B	1.1985	1.2387	0.0103	0.161*
H15C	1.0213	1.3544	0.0402	0.161*
C16	0.6734 (3)	0.6529 (2)	0.18118 (13)	0.0562 (5)
C17	0.7294 (4)	0.5084 (3)	0.18933 (17)	0.0736 (7)
H17	0.8360	0.4553	0.2118	0.088*
C18	0.6240 (6)	0.4413 (4)	0.1634 (2)	0.0970 (10)
H18	0.6617	0.3426	0.1690	0.116*
C19	0.4665 (6)	0.5173 (5)	0.13009 (19)	0.0973 (11)
C20	0.4129 (5)	0.6620 (4)	0.12418 (18)	0.0931 (9)
H20	0.3046	0.7151	0.1032	0.112*
C21	0.5151 (4)	0.7320 (3)	0.14848 (16)	0.0724 (7)
H21	0.4774	0.8308	0.1428	0.087*
C22	0.3564 (7)	0.4413 (5)	0.1003 (2)	0.152 (2)
H22A	0.2336	0.4791	0.1223	0.227*
H22B	0.4016	0.3415	0.1192	0.227*
H22C	0.3644	0.4555	0.0407	0.227*
H1	0.454 (2)	0.725 (2)	0.4405 (9)	0.050 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.03462 (19)	0.03290 (18)	0.0518 (2)	−0.01460 (14)	−0.00187 (14)	−0.00726 (14)
S1	0.0497 (3)	0.0674 (4)	0.0815 (4)	−0.0103 (3)	−0.0107 (3)	−0.0296 (3)
S2	0.0511 (3)	0.0700 (4)	0.0695 (4)	−0.0252 (3)	0.0033 (3)	0.0047 (3)
P1	0.0398 (3)	0.0550 (3)	0.0595 (3)	−0.0211 (2)	−0.0010 (2)	−0.0099 (3)
O1	0.0508 (9)	0.0682 (10)	0.0724 (10)	−0.0338 (8)	−0.0172 (7)	0.0134 (8)
O2	0.0550 (9)	0.0629 (9)	0.0610 (9)	−0.0280 (7)	0.0116 (7)	−0.0162 (7)
N1	0.0388 (8)	0.0465 (9)	0.0529 (9)	−0.0193 (7)	−0.0021 (7)	−0.0079 (7)
N2	0.0369 (8)	0.0369 (8)	0.0579 (10)	−0.0161 (7)	0.0019 (7)	−0.0051 (7)
C1	0.0440 (11)	0.0584 (12)	0.0579 (12)	−0.0248 (10)	0.0044 (9)	−0.0209 (10)
C2	0.0703 (17)	0.094 (2)	0.093 (2)	−0.0299 (15)	−0.0153 (15)	−0.0417 (16)
C3	0.0655 (14)	0.0489 (12)	0.0706 (14)	−0.0302 (11)	0.0049 (11)	−0.0222 (10)
C4	0.0523 (12)	0.0564 (13)	0.0676 (14)	−0.0197 (10)	−0.0186 (11)	−0.0003 (11)
C5	0.0453 (12)	0.0472 (12)	0.0810 (16)	−0.0100 (9)	−0.0140 (11)	−0.0058 (11)
C6	0.0502 (12)	0.0365 (10)	0.0670 (13)	−0.0176 (9)	0.0088 (10)	−0.0150 (9)
C7	0.0739 (16)	0.0372 (11)	0.0992 (19)	−0.0154 (11)	0.0037 (14)	−0.0134 (12)
C8	0.0630 (15)	0.0575 (14)	0.0740 (16)	−0.0199 (11)	0.0196 (12)	−0.0154 (12)
C9	0.0511 (12)	0.0509 (12)	0.0578 (13)	−0.0229 (10)	−0.0060 (10)	−0.0034 (10)
C10	0.0540 (13)	0.0792 (16)	0.0664 (14)	−0.0344 (12)	−0.0110 (11)	0.0047 (12)
C11	0.0684 (16)	0.0855 (18)	0.0819 (18)	−0.0482 (14)	−0.0039 (14)	0.0006 (14)
C12	0.0870 (18)	0.0644 (15)	0.0668 (16)	−0.0392 (14)	0.0014 (14)	−0.0026 (12)
C13	0.108 (2)	0.0776 (18)	0.0716 (17)	−0.0462 (17)	−0.0337 (16)	0.0127 (14)
C14	0.0813 (17)	0.0724 (16)	0.0822 (18)	−0.0450 (14)	−0.0304 (14)	0.0095 (14)
C15	0.144 (3)	0.106 (2)	0.087 (2)	−0.076 (2)	−0.005 (2)	0.0168 (18)
C16	0.0642 (14)	0.0647 (14)	0.0456 (11)	−0.0305 (12)	0.0101 (10)	−0.0167 (10)
C17	0.0858 (18)	0.0643 (15)	0.0735 (17)	−0.0294 (14)	0.0077 (14)	−0.0201 (13)
C18	0.142 (3)	0.084 (2)	0.085 (2)	−0.062 (2)	0.014 (2)	−0.0307 (17)
C19	0.133 (3)	0.134 (3)	0.0614 (17)	−0.086 (3)	0.0001 (18)	−0.0301 (18)
C20	0.100 (2)	0.132 (3)	0.0655 (17)	−0.053 (2)	−0.0194 (16)	−0.0189 (18)
C21	0.0818 (18)	0.0788 (17)	0.0612 (15)	−0.0287 (14)	−0.0103 (13)	−0.0133 (13)
C22	0.223 (5)	0.224 (5)	0.090 (2)	−0.169 (5)	−0.011 (3)	−0.040 (3)

Geometric parameters (Å, º) top

Ni1—N1	1.9135 (16)	C7—H7C	0.9600
Ni1—N1ⁱ	1.9135 (16)	C8—H8A	0.9600
Ni1—N2ⁱ	1.9364 (15)	C8—H8B	0.9600
Ni1—N2	1.9364 (15)	C8—H8C	0.9600
S1—P1	1.9505 (8)	C9—C10	1.366 (3)
S2—P1	1.9575 (8)	C9—C14	1.367 (3)
P1—O1	1.6131 (14)	C10—C11	1.377 (3)
P1—O2	1.6216 (16)	C10—H10	0.9300
O1—C9	1.395 (3)	C11—C12	1.371 (4)
O2—C16	1.396 (3)	C11—H11	0.9300
N1—C1	1.285 (2)	C12—C13	1.369 (4)
N1—C4	1.476 (3)	C12—C15	1.522 (4)
N2—C5	1.483 (3)	C13—C14	1.388 (3)
N2—C6	1.497 (3)	C13—H13	0.9300
C1—C3	1.484 (3)	C14—H14	0.9300
C1—C2	1.500 (3)	C15—H15A	0.9600
C2—H2A	0.9600	C15—H15B	0.9600
C2—H2B	0.9600	C15—H15C	0.9600
C2—H2C	0.9600	C16—C17	1.360 (3)
C3—C6ⁱ	1.518 (3)	C16—C21	1.377 (4)
C3—H3A	0.9700	C17—C18	1.396 (4)
C3—H3B	0.9700	C17—H17	0.9300
C4—C5	1.494 (3)	C18—C19	1.371 (5)
C4—H4A	0.9700	C18—H18	0.9300
C4—H4B	0.9700	C19—C20	1.365 (5)
C5—H5A	0.9700	C19—C22	1.525 (4)
C5—H5B	0.9700	C20—C21	1.385 (4)
C6—C3ⁱ	1.518 (3)	C20—H20	0.9300
C6—C8	1.519 (3)	C21—H21	0.9300
C6—C7	1.537 (3)	C22—H22A	0.9600
C7—H7A	0.9600	C22—H22B	0.9600
C7—H7B	0.9600	C22—H22C	0.9600

N1—Ni1—N1ⁱ	180.000 (1)	H7A—C7—H7B	109.5
N1—Ni1—N2ⁱ	94.15 (7)	C6—C7—H7C	109.5
N1ⁱ—Ni1—N2ⁱ	85.85 (7)	H7A—C7—H7C	109.5
N1—Ni1—N2	85.85 (7)	H7B—C7—H7C	109.5
N1ⁱ—Ni1—N2	94.15 (7)	C6—C8—H8A	109.5
N2ⁱ—Ni1—N2	180.000 (1)	C6—C8—H8B	109.5
O1—P1—O2	96.75 (9)	H8A—C8—H8B	109.5
O1—P1—S1	112.77 (7)	C6—C8—H8C	109.5
O2—P1—S1	111.07 (7)	H8A—C8—H8C	109.5
O1—P1—S2	106.04 (6)	H8B—C8—H8C	109.5
O2—P1—S2	110.96 (7)	C10—C9—C14	120.0 (2)
S1—P1—S2	117.27 (4)	C10—C9—O1	115.11 (19)
C9—O1—P1	127.94 (14)	C14—C9—O1	124.9 (2)
C16—O2—P1	122.66 (13)	C9—C10—C11	120.1 (2)
C1—N1—C4	119.78 (18)	C9—C10—H10	120.0
C1—N1—Ni1	128.75 (15)	C11—C10—H10	120.0
C4—N1—Ni1	111.31 (12)	C12—C11—C10	121.6 (2)
C5—N2—C6	115.10 (16)	C12—C11—H11	119.2
C5—N2—Ni1	107.47 (12)	C10—C11—H11	119.2
C6—N2—Ni1	119.17 (13)	C13—C12—C11	117.2 (2)
C5—N2—H1	106.3 (14)	C13—C12—C15	120.9 (3)
C6—N2—H1	107.6 (14)	C11—C12—C15	121.9 (3)
Ni1—N2—H1	99.3 (14)	C12—C13—C14	122.3 (2)
N1—C1—C3	120.94 (19)	C12—C13—H13	118.8
N1—C1—C2	123.7 (2)	C14—C13—H13	118.8
C3—C1—C2	115.32 (19)	C9—C14—C13	118.8 (2)
C1—C2—H2A	109.5	C9—C14—H14	120.6
C1—C2—H2B	109.5	C13—C14—H14	120.6
H2A—C2—H2B	109.5	C12—C15—H15A	109.5
C1—C2—H2C	109.5	C12—C15—H15B	109.5
H2A—C2—H2C	109.5	H15A—C15—H15B	109.5
H2B—C2—H2C	109.5	C12—C15—H15C	109.5
C1—C3—C6ⁱ	117.74 (17)	H15A—C15—H15C	109.5
C1—C3—H3A	107.9	H15B—C15—H15C	109.5
C6ⁱ—C3—H3A	107.9	C17—C16—C21	120.8 (2)
C1—C3—H3B	107.9	C17—C16—O2	118.9 (2)
C6ⁱ—C3—H3B	107.9	C21—C16—O2	120.3 (2)
H3A—C3—H3B	107.2	C16—C17—C18	118.9 (3)
N1—C4—C5	106.65 (18)	C16—C17—H17	120.6
N1—C4—H4A	110.4	C18—C17—H17	120.6
C5—C4—H4A	110.4	C19—C18—C17	121.7 (3)
N1—C4—H4B	110.4	C19—C18—H18	119.2
C5—C4—H4B	110.4	C17—C18—H18	119.2
H4A—C4—H4B	108.6	C20—C19—C18	117.9 (3)
N2—C5—C4	106.26 (17)	C20—C19—C22	121.5 (4)
N2—C5—H5A	110.5	C18—C19—C22	120.6 (4)
C4—C5—H5A	110.5	C19—C20—C21	121.9 (3)
N2—C5—H5B	110.5	C19—C20—H20	119.1
C4—C5—H5B	110.5	C21—C20—H20	119.1
H5A—C5—H5B	108.7	C16—C21—C20	118.9 (3)
N2—C6—C3ⁱ	106.09 (16)	C16—C21—H21	120.6
N2—C6—C8	110.29 (17)	C20—C21—H21	120.6
C3ⁱ—C6—C8	112.3 (2)	C19—C22—H22A	109.5
N2—C6—C7	110.74 (19)	C19—C22—H22B	109.5
C3ⁱ—C6—C7	106.99 (18)	H22A—C22—H22B	109.5
C8—C6—C7	110.33 (18)	C19—C22—H22C	109.5
C6—C7—H7A	109.5	H22A—C22—H22C	109.5
C6—C7—H7B	109.5	H22B—C22—H22C	109.5

O2—P1—O1—C9	61.8 (2)	C5—N2—C6—C7	−55.6 (2)
S1—P1—O1—C9	−54.5 (2)	Ni1—N2—C6—C7	174.50 (14)
S2—P1—O1—C9	175.93 (17)	P1—O1—C9—C10	171.21 (17)
O1—P1—O2—C16	−178.20 (17)	P1—O1—C9—C14	−10.6 (4)
S1—P1—O2—C16	−60.61 (18)	C14—C9—C10—C11	−0.4 (4)
S2—P1—O2—C16	71.73 (17)	O1—C9—C10—C11	177.9 (2)
N2ⁱ—Ni1—N1—C1	10.52 (18)	C9—C10—C11—C12	−0.2 (4)
N2—Ni1—N1—C1	−169.48 (18)	C10—C11—C12—C13	0.4 (4)
N2ⁱ—Ni1—N1—C4	−174.05 (14)	C10—C11—C12—C15	179.4 (3)
N2—Ni1—N1—C4	5.95 (14)	C11—C12—C13—C14	−0.1 (5)
N1ⁱ—Ni1—N2—C5	−157.85 (14)	C15—C12—C13—C14	−179.2 (3)
N1ⁱ—Ni1—N2—C6	−24.62 (14)	C10—C9—C14—C13	0.6 (4)
C4—N1—C1—C3	177.86 (19)	O1—C9—C14—C13	−177.5 (2)
Ni1—N1—C1—C3	−7.0 (3)	C12—C13—C14—C9	−0.4 (5)
C4—N1—C1—C2	−3.3 (3)	P1—O2—C16—C17	−101.5 (2)
Ni1—N1—C1—C2	171.82 (17)	P1—O2—C16—C21	81.8 (2)
N1—C1—C3—C6ⁱ	−33.5 (3)	C21—C16—C17—C18	0.4 (4)
C2—C1—C3—C6ⁱ	147.6 (2)	O2—C16—C17—C18	−176.3 (2)
C1—N1—C4—C5	143.51 (19)	C16—C17—C18—C19	0.1 (4)
Ni1—N1—C4—C5	−32.4 (2)	C17—C18—C19—C20	−1.2 (5)
C6—N2—C5—C4	179.55 (17)	C17—C18—C19—C22	178.5 (3)
Ni1—N2—C5—C4	−45.1 (2)	C18—C19—C20—C21	1.9 (5)
N1—C4—C5—N2	49.9 (2)	C22—C19—C20—C21	−177.8 (3)
C5—N2—C6—C3ⁱ	−171.36 (17)	C17—C16—C21—C20	0.2 (4)
Ni1—N2—C6—C3ⁱ	58.76 (19)	O2—C16—C21—C20	176.9 (2)
C5—N2—C6—C8	66.8 (2)	C19—C20—C21—C16	−1.4 (4)
Ni1—N2—C6—C8	−63.1 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₆H₃₂N₄)](C₁₄H₁₄O₂PS₂)₂
M_r	957.85
Crystal system, space group	Triclinic, P1
Temperature (K)	278
a, b, c (Å)	8.0044 (6), 10.0996 (8), 16.4004 (12)
α, β, γ (°)	80.418 (1), 81.333 (1), 69.836 (1)
V (Å³)	1220.95 (16)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.18 × 0.14 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.888, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	6525, 4305, 3756
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.085, 1.04
No. of reflections	4305
No. of parameters	273
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.34

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008).

Acknowledgements

This project was supported by the Education Committee of Sichuan Province of China (project No. 2006 A110, 07ZA161), the Science and Technology Office of Zigong City of China (project No. 08X01), and the University Key Laboratory of Corrosin and Protection of Materials of Sichuan Province of China (project No. 2008 C L04).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xie, B., Zou, L.-K., He, Y.-G., Feng, J.-S. & Zhang, X.-L. (2008). Acta Cryst. E64, m622. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.