(meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetra­azacyclo­tetra­deca­ne)nickel(II) bis­(O,O′-dibenzyl dithio­phosphate)

Xie, B.; Zou, L.-K.; He, Y.-G.; Feng, J.-S.; Zhang, X.-L.

doi:10.1107/S1600536808008398

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m622

doi:10.1107/S1600536808008398

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(meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane)nickel(II) bis(O,O′-dibenzyl dithiophosphate)

Bin Xie,^a ^* Li-Ke Zou,^a Yi-Guo He,^a Jian-Shen Feng ^a and Xiu-Lan Zhang ^a

^aDepartment of Chemistry, Sichuan University of Science & Engineering, Zigong, Sichuan 643000, People's Republic of China
^*Correspondence e-mail: zoulike@yahoo.com.cn

(Received 15 March 2008; accepted 28 March 2008; online 4 April 2008)

In the title salt-type 1:2 adduct, [Ni(C₁₆H₃₆N₄)](C₁₄H₁₄O₂PS₂)₂ or [Ni(tet-a)][S₂P(OCH₂Ph)₂]₂, where tet-a is meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, the [Ni(tet-a)]²⁺ complex cation exhibits a relatively undistorted square-planar geometry about the Ni atom, which lies on an inversion centre and is coordinated by four macrocyclic N atoms. The two O,O′-bis(2-phenylmethyl) dithiophosphate anions act as counter-ions to balance the charge and they interact with the complex through N—H⋯S hydrogen bonds. Important geometric data include Ni—N distances of 1.958 (3) and 1.963 (3) Å.

Related literature

For related literature, see: Burchell et al. (2000 ); Ali et al. (2004 ); Allen (2002 ); Li et al. (2006 ); Liu et al. (1997 ).

Experimental

Crystal data

[Ni(C₁₆H₃₆N₄)](C₁₄H₁₄O₂PS₂)₂
M_r = 961.88
Monoclinic, P 2₁ /c
a = 16.371 (5) Å
b = 14.917 (5) Å
c = 9.964 (4) Å
β = 103.11 (3)°
V = 2369.9 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.70 mm⁻¹
T = 290 (2) K
0.40 × 0.38 × 0.36 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.768, T_max = 0.787
5571 measured reflections
4393 independent reflections
2880 reflections with I > 2σ(I)
R_int = 0.021
3 standard reflections every 300 reflections intensity decay: 1.1%

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.127
S = 1.01
4393 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1	0.91	2.61	3.390 (3)	144
N2—H2⋯S2ⁱ	0.91	2.50	3.394 (3)	169
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008398/dn2324sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008398/dn2324Isup2.hkl

checkCIF report

Comment top

Considerable interest in the chemistry of the O,O'-dialkyl dithiophosphate complexes of transition metal results from their value to industry, namely, as anti-oxidants, additives to lubricating oils, flotation reagents, insecticides(Liu et al.,1997;Li et al.,2006).We report here the synthesis and crystal structure of salt-type adduct [Ni(tet-a)][S₂P(OCH₂Ph)₂]₂ (tet-a=meso-5,5,7,12,12,14-hexamethyl- 1,4,8,11-tetraazacyclotetradecane, a tetradentate macrocyclic nitrogen base (Burchell et al.,2000; Ali et al.,2004 ))

The Ni^II in the complex cation [Ni(tet-a)]²⁺ lies on an inversion center and is coordinated by four nitrogen atoms of teteaaza macrocycle in undistorted square-planar geometry (Fig.1). The bond lengths and angles within the complex may be considered normal in comparison with the Cambridge Structural Database results (Allen, 2002).

The two O,O'- di(2-phenylmethyl) dithiophosphates act as counter-ions to balance the charge and they interact with the complex through N—H···S hydrogen bonds (Table 1).

Related literature top

For related literature, see: Burchell et al. (2000); Ali et al. (2004); Allen (2002); Li et al. (2006); Liu et al. (1997).

Experimental top

A hot solution of tet-a.2H₂O (0.77 g, 2 mmol) and Ni(OAc)₂.2H₂O (0.25 g, 1 mmol) in 20 ml me thanol was quickly added to a hot solution of (PhCH₂O)₂PSSNH₂(C₂H₅)₂(0.77 g, 2 mmol) in 20 ml me thanol. The mixture was refluxed for 6 h, then cooled to room temperature, the orange-red precipitate was collected by filtration, washed with small amounts of methanol.A solution of adduct (1) in DMSO was kept at room temperature, and red block crystals suitable for X-ray diffraction studies were obtained in eight months,.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A View of the title compound showing the atom-labelling scheme.Only one of the two anions is represented for clarity.Displacement ellipsoids are drawn at the 30% probability level. Hydrogen-bonds are shown as dashed lines. For the sake of clarity, H atoms bonded to C atoms have been omitted. H atoms are represented as small spheres of arbitrary radii. [Symmetry code: (i) -x + 1, -y + 1, -z].

(meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11- tetraazacyclotetradecane)nickel(II) bis(O,O'-dibenzyl dithiophosphate) top

Crystal data top

[Ni(C₁₆H₃₆N₄)](C₁₄H₁₄O₂PS₂)₂	F(000) = 1020
M_r = 961.88	D_x = 1.348 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19 reflections
a = 16.371 (5) Å	θ = 4.4–5.5°
b = 14.917 (5) Å	µ = 0.70 mm⁻¹
c = 9.964 (4) Å	T = 290 K
β = 103.11 (3)°	Block, red
V = 2369.9 (15) Å³	0.40 × 0.38 × 0.36 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	2880 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 25.5°, θ_min = 1.3°
ω/2θ scans	h = −7→19
Absorption correction: ψ scan (North et al., 1968)	k = −18→0
T_min = 0.768, T_max = 0.787	l = −12→11
5571 measured reflections	3 standard reflections every 300 reflections
4393 independent reflections	intensity decay: 1.1%

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0689P)²] where P = (F_o² + 2F_c²)/3
4393 reflections	(Δ/σ)_max < 0.001
275 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Ni(C₁₆H₃₆N₄)](C₁₄H₁₄O₂PS₂)₂	V = 2369.9 (15) Å³
M_r = 961.88	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.371 (5) Å	µ = 0.70 mm⁻¹
b = 14.917 (5) Å	T = 290 K
c = 9.964 (4) Å	0.40 × 0.38 × 0.36 mm
β = 103.11 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2880 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.021
T_min = 0.768, T_max = 0.787	3 standard reflections every 300 reflections
5571 measured reflections	intensity decay: 1.1%
4393 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.01	Δρ_max = 0.52 e Å⁻³
4393 reflections	Δρ_min = −0.34 e Å⁻³
275 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	0.0000	0.02975 (18)
S1	0.39590 (6)	0.45749 (7)	0.26928 (12)	0.0569 (3)
S2	0.28652 (6)	0.64383 (7)	0.13356 (11)	0.0498 (3)
P1	0.29136 (6)	0.52753 (7)	0.22790 (10)	0.0406 (3)
O1	0.26427 (15)	0.53665 (18)	0.3726 (3)	0.0509 (7)
O2	0.21601 (15)	0.47114 (17)	0.1325 (3)	0.0521 (7)
N1	0.57052 (16)	0.53521 (17)	0.1790 (3)	0.0341 (7)
H1	0.5357	0.5294	0.2379	0.041*
N2	0.55476 (16)	0.38269 (17)	0.0308 (3)	0.0332 (6)
H2	0.5975	0.3845	−0.0138	0.040*
C1	0.6346 (2)	0.4648 (2)	0.2251 (4)	0.0543 (12)
H1A	0.6539	0.4663	0.3245	0.065*
H1B	0.6824	0.4747	0.1844	0.065*
C2	0.5955 (2)	0.3765 (2)	0.1806 (4)	0.0478 (10)
H2A	0.5540	0.3619	0.2330	0.057*
H2B	0.6378	0.3298	0.1960	0.057*
C3	0.5074 (2)	0.2981 (2)	−0.0165 (3)	0.0353 (8)
H3	0.4636	0.2913	0.0354	0.042*
C4	0.4652 (2)	0.3050 (2)	−0.1675 (4)	0.0397 (9)
H4A	0.4439	0.2462	−0.1989	0.048*
H4B	0.5077	0.3204	−0.2174	0.048*
C5	0.5636 (2)	0.2146 (2)	0.0096 (4)	0.0452 (9)
H5A	0.6067	0.2194	−0.0413	0.068*
H5B	0.5304	0.1621	−0.0197	0.068*
H5C	0.5889	0.2101	0.1062	0.068*
C6	0.6063 (2)	0.6282 (2)	0.2081 (4)	0.0359 (8)
C7	0.6734 (2)	0.6441 (3)	0.1263 (4)	0.0542 (11)
H7A	0.6523	0.6262	0.0323	0.081*
H7B	0.7225	0.6096	0.1658	0.081*
H7C	0.6877	0.7066	0.1293	0.081*
C8	0.6443 (2)	0.6385 (3)	0.3636 (4)	0.0543 (11)
H8A	0.6602	0.6998	0.3838	0.081*
H8B	0.6928	0.6008	0.3896	0.081*
H8C	0.6035	0.6212	0.4144	0.081*
C9	0.1889 (3)	0.5872 (3)	0.3782 (4)	0.0624 (12)
H9A	0.1446	0.5736	0.2982	0.075*
H9B	0.2003	0.6510	0.3783	0.075*
C10	0.1620 (2)	0.5621 (3)	0.5064 (4)	0.0511 (10)
C11	0.1766 (3)	0.6179 (3)	0.6203 (5)	0.0639 (12)
H11	0.2020	0.6734	0.6175	0.077*
C12	0.1527 (3)	0.5897 (5)	0.7399 (5)	0.0884 (18)
H12	0.1623	0.6266	0.8171	0.106*
C13	0.1153 (4)	0.5082 (6)	0.7433 (7)	0.103 (2)
H13	0.0995	0.4899	0.8230	0.123*
C14	0.1010 (4)	0.4537 (5)	0.6318 (8)	0.108 (2)
H14	0.0759	0.3980	0.6349	0.130*
C15	0.1237 (3)	0.4810 (4)	0.5149 (6)	0.0822 (15)
H15	0.1130	0.4435	0.4383	0.099*
C16	0.2008 (2)	0.3800 (3)	0.1649 (5)	0.0604 (12)
H16A	0.1953	0.3756	0.2596	0.072*
H16B	0.2473	0.3425	0.1542	0.072*
C17	0.1214 (2)	0.3495 (2)	0.0688 (4)	0.0472 (10)
C18	0.0461 (3)	0.3895 (3)	0.0682 (5)	0.0681 (13)
H18	0.0439	0.4365	0.1287	0.082*
C19	−0.0272 (3)	0.3613 (4)	−0.0213 (5)	0.0795 (16)
H19	−0.0781	0.3884	−0.0193	0.095*
C20	−0.0245 (3)	0.2952 (4)	−0.1100 (6)	0.0853 (18)
H20	−0.0738	0.2751	−0.1682	0.102*
C21	0.0503 (4)	0.2567 (4)	−0.1159 (6)	0.108 (2)
H21	0.0522	0.2126	−0.1811	0.130*
C22	0.1229 (3)	0.2831 (3)	−0.0256 (6)	0.0808 (16)
H22	0.1734	0.2557	−0.0286	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0297 (3)	0.0263 (3)	0.0308 (3)	0.0014 (2)	0.0017 (2)	0.0013 (3)
S1	0.0404 (5)	0.0557 (6)	0.0758 (8)	0.0085 (5)	0.0157 (5)	0.0121 (6)
S2	0.0506 (6)	0.0459 (6)	0.0535 (6)	−0.0007 (4)	0.0129 (5)	0.0074 (5)
P1	0.0349 (5)	0.0421 (5)	0.0440 (6)	−0.0003 (4)	0.0070 (4)	0.0019 (4)
O1	0.0459 (14)	0.0648 (17)	0.0443 (16)	0.0157 (13)	0.0152 (12)	0.0131 (13)
O2	0.0455 (14)	0.0413 (14)	0.0633 (18)	−0.0079 (11)	−0.0011 (13)	0.0018 (13)
N1	0.0367 (14)	0.0292 (14)	0.0336 (16)	0.0000 (12)	0.0023 (12)	0.0011 (12)
N2	0.0332 (14)	0.0297 (15)	0.0358 (16)	0.0036 (11)	0.0059 (12)	0.0022 (12)
C1	0.052 (2)	0.037 (2)	0.059 (3)	0.0101 (17)	−0.019 (2)	−0.0037 (19)
C2	0.058 (2)	0.035 (2)	0.039 (2)	0.0084 (17)	−0.0113 (18)	0.0016 (17)
C3	0.0396 (18)	0.0274 (16)	0.038 (2)	−0.0049 (14)	0.0082 (15)	−0.0018 (15)
C4	0.0458 (19)	0.0307 (18)	0.041 (2)	−0.0024 (15)	0.0071 (16)	−0.0022 (16)
C5	0.060 (2)	0.0301 (19)	0.044 (2)	0.0053 (16)	0.0098 (18)	0.0000 (17)
C6	0.0390 (18)	0.0301 (18)	0.037 (2)	−0.0041 (14)	0.0046 (15)	−0.0051 (15)
C7	0.041 (2)	0.056 (2)	0.065 (3)	−0.0041 (18)	0.0109 (19)	0.006 (2)
C8	0.058 (2)	0.050 (2)	0.045 (2)	0.0027 (19)	−0.0075 (19)	−0.0090 (19)
C9	0.060 (2)	0.075 (3)	0.056 (3)	0.025 (2)	0.020 (2)	0.014 (2)
C10	0.044 (2)	0.061 (3)	0.050 (3)	0.019 (2)	0.0147 (18)	0.011 (2)
C11	0.058 (3)	0.073 (3)	0.060 (3)	0.019 (2)	0.012 (2)	−0.001 (2)
C12	0.083 (4)	0.128 (5)	0.055 (3)	0.050 (4)	0.018 (3)	−0.003 (3)
C13	0.097 (4)	0.138 (6)	0.091 (5)	0.063 (4)	0.061 (4)	0.053 (5)
C14	0.114 (5)	0.089 (5)	0.146 (6)	0.021 (4)	0.080 (5)	0.043 (5)
C15	0.095 (4)	0.077 (4)	0.086 (4)	−0.002 (3)	0.043 (3)	0.001 (3)
C16	0.055 (2)	0.039 (2)	0.081 (3)	−0.0046 (18)	0.004 (2)	0.005 (2)
C17	0.043 (2)	0.038 (2)	0.059 (3)	−0.0055 (17)	0.0095 (18)	0.0008 (19)
C18	0.060 (3)	0.079 (3)	0.064 (3)	0.020 (2)	0.010 (2)	−0.016 (3)
C19	0.043 (2)	0.118 (5)	0.076 (4)	0.011 (3)	0.009 (2)	0.010 (3)
C20	0.066 (3)	0.060 (3)	0.114 (5)	−0.018 (3)	−0.014 (3)	0.002 (3)
C21	0.113 (5)	0.062 (3)	0.126 (5)	0.007 (3)	−0.023 (4)	−0.044 (4)
C22	0.064 (3)	0.062 (3)	0.109 (4)	0.012 (2)	0.006 (3)	−0.021 (3)

Geometric parameters (Å, º) top

Ni1—N2	1.958 (3)	C7—H7C	0.9600
Ni1—N1	1.963 (3)	C8—H8A	0.9600
S1—P1	1.9674 (14)	C8—H8B	0.9600
S2—P1	1.9661 (15)	C8—H8C	0.9600
P1—O1	1.608 (3)	C9—C10	1.490 (6)
P1—O2	1.613 (3)	C9—H9A	0.9700
O1—C9	1.459 (4)	C9—H9B	0.9700
O2—C16	1.432 (4)	C10—C15	1.374 (7)
N1—C1	1.482 (4)	C10—C11	1.385 (6)
N1—C6	1.509 (4)	C11—C12	1.400 (7)
N1—H1	0.9100	C11—H11	0.9300
N2—C2	1.493 (4)	C12—C13	1.366 (9)
N2—C3	1.501 (4)	C12—H12	0.9300
N2—H2	0.9100	C13—C14	1.354 (9)
C1—C2	1.488 (5)	C13—H13	0.9300
C1—H1A	0.9700	C14—C15	1.363 (8)
C1—H1B	0.9700	C14—H14	0.9300
C2—H2A	0.9700	C15—H15	0.9300
C2—H2B	0.9700	C16—C17	1.500 (5)
C3—C4	1.510 (4)	C16—H16A	0.9700
C3—C5	1.535 (4)	C16—H16B	0.9700
C3—H3	0.9800	C17—C18	1.369 (5)
C4—C6ⁱ	1.520 (4)	C17—C22	1.370 (6)
C4—H4A	0.9700	C18—C19	1.388 (6)
C4—H4B	0.9700	C18—H18	0.9300
C5—H5A	0.9600	C19—C20	1.332 (7)
C5—H5B	0.9600	C19—H19	0.9300
C5—H5C	0.9600	C20—C21	1.366 (7)
C6—C4ⁱ	1.520 (4)	C20—H20	0.9300
C6—C7	1.528 (5)	C21—C22	1.376 (6)
C6—C8	1.541 (5)	C21—H21	0.9300
C7—H7A	0.9600	C22—H22	0.9300
C7—H7B	0.9600

N2—Ni1—N1	86.71 (11)	C6—C7—H7B	109.5
N2ⁱ—Ni1—N1	93.29 (11)	H7A—C7—H7B	109.5
O1—P1—O2	104.07 (15)	C6—C7—H7C	109.5
O1—P1—S2	111.40 (12)	H7A—C7—H7C	109.5
O2—P1—S2	103.65 (11)	H7B—C7—H7C	109.5
O1—P1—S1	105.11 (11)	C6—C8—H8A	109.5
O2—P1—S1	111.05 (11)	C6—C8—H8B	109.5
S2—P1—S1	120.50 (7)	H8A—C8—H8B	109.5
C9—O1—P1	119.1 (2)	C6—C8—H8C	109.5
C16—O2—P1	120.7 (2)	H8A—C8—H8C	109.5
C1—N1—C6	112.0 (2)	H8B—C8—H8C	109.5
C1—N1—Ni1	108.7 (2)	O1—C9—C10	108.6 (3)
C6—N1—Ni1	122.9 (2)	O1—C9—H9A	110.0
C1—N1—H1	103.6	C10—C9—H9A	110.0
C6—N1—H1	103.6	O1—C9—H9B	110.0
Ni1—N1—H1	103.6	C10—C9—H9B	110.0
C2—N2—C3	110.1 (2)	H9A—C9—H9B	108.3
C2—N2—Ni1	107.3 (2)	C15—C10—C11	118.4 (4)
C3—N2—Ni1	121.11 (19)	C15—C10—C9	120.1 (4)
C2—N2—H2	105.8	C11—C10—C9	121.5 (4)
C3—N2—H2	105.8	C10—C11—C12	119.2 (5)
Ni1—N2—H2	105.8	C10—C11—H11	120.4
N1—C1—C2	108.0 (3)	C12—C11—H11	120.4
N1—C1—H1A	110.1	C13—C12—C11	120.1 (6)
C2—C1—H1A	110.1	C13—C12—H12	119.9
N1—C1—H1B	110.1	C11—C12—H12	119.9
C2—C1—H1B	110.1	C14—C13—C12	120.6 (6)
H1A—C1—H1B	108.4	C14—C13—H13	119.7
C1—C2—N2	107.9 (3)	C12—C13—H13	119.7
C1—C2—H2A	110.1	C13—C14—C15	119.5 (6)
N2—C2—H2A	110.1	C13—C14—H14	120.2
C1—C2—H2B	110.1	C15—C14—H14	120.2
N2—C2—H2B	110.1	C14—C15—C10	122.2 (6)
H2A—C2—H2B	108.4	C14—C15—H15	118.9
N2—C3—C4	110.0 (3)	C10—C15—H15	118.9
N2—C3—C5	112.4 (2)	O2—C16—C17	108.3 (3)
C4—C3—C5	110.3 (3)	O2—C16—H16A	110.0
N2—C3—H3	108.0	C17—C16—H16A	110.0
C4—C3—H3	108.0	O2—C16—H16B	110.0
C5—C3—H3	108.0	C17—C16—H16B	110.0
C3—C4—C6ⁱ	117.4 (3)	H16A—C16—H16B	108.4
C3—C4—H4A	107.9	C18—C17—C22	118.0 (4)
C6ⁱ—C4—H4A	107.9	C18—C17—C16	121.3 (4)
C3—C4—H4B	107.9	C22—C17—C16	120.6 (4)
C6ⁱ—C4—H4B	107.9	C17—C18—C19	121.1 (4)
H4A—C4—H4B	107.2	C17—C18—H18	119.4
C3—C5—H5A	109.5	C19—C18—H18	119.4
C3—C5—H5B	109.5	C20—C19—C18	119.8 (5)
H5A—C5—H5B	109.5	C20—C19—H19	120.1
C3—C5—H5C	109.5	C18—C19—H19	120.1
H5A—C5—H5C	109.5	C19—C20—C21	120.3 (5)
H5B—C5—H5C	109.5	C19—C20—H20	119.8
N1—C6—C4ⁱ	108.0 (2)	C21—C20—H20	119.8
N1—C6—C7	109.6 (3)	C20—C21—C22	120.1 (5)
C4ⁱ—C6—C7	111.1 (3)	C20—C21—H21	120.0
N1—C6—C8	109.6 (3)	C22—C21—H21	120.0
C4ⁱ—C6—C8	108.3 (3)	C17—C22—C21	120.6 (5)
C7—C6—C8	110.3 (3)	C17—C22—H22	119.7
C6—C7—H7A	109.5	C21—C22—H22	119.7

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1	0.91	2.61	3.390 (3)	144
N2—H2···S2ⁱ	0.91	2.50	3.394 (3)	169

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₆H₃₆N₄)](C₁₄H₁₄O₂PS₂)₂
M_r	961.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	290
a, b, c (Å)	16.371 (5), 14.917 (5), 9.964 (4)
β (°)	103.11 (3)
V (Å³)	2369.9 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.40 × 0.38 × 0.36

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.768, 0.787
No. of measured, independent and observed [I > 2σ(I)] reflections	5571, 4393, 2880
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.127, 1.01
No. of reflections	4393
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.34

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1	0.91	2.61	3.390 (3)	144.1
N2—H2···S2ⁱ	0.91	2.50	3.394 (3)	168.5

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

Financial assistance from the Science and Technology Office of Zigong City, China (Project No. 06 G2045 and 07GX008) is gratefully acknowledged.

References

Ali, M., Ray, A., Sheldrick, W. S., Mayer-Figge, H., Gao, S. & Sahmesd, A. I. (2004). New J. Chem. 28, 412–417. Web of Science CSD CrossRef CAS Google Scholar
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burchell, C. J., Ferguson, G., Lough, A. J. & Glidewell, C. (2000). Acta Cryst. B56, 1054–1062. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Li, Z., Li, J. & Du, S. (2006). J. Mol. Struct. 783, 116–121. Web of Science CSD CrossRef CAS Google Scholar
Liu, C. W., Pitts, J. T. & Fackler, J. P. (1997). Polyhedron, 16, 3899–3909. CSD CrossRef CAS Web of Science Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 5| May 2008| Page m622

doi:10.1107/S1600536808008398

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(meso-5,5,7,12,12,14-Hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­deca­ne)nickel(II) bis­­(O,O′-di­benzyl di­thio­phosphate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

(meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane)nickel(II) bis(O,O′-dibenzyl dithiophosphate)