(meso-5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetra-azacyclo-tetra-deca-4,11-diene)nickel(II) bis-[O,O'-bis(4-methyl-phen-yl) dithio-phosphate].

In the title compound, [Ni(C(16)H(32)N(4))](C(14)H(14)O(2)PS(2))(2) or [Ni(trans[14]dien)][S(2)P(OC(6)H(4)Me-4)(2)](2), where trans[14]dien is meso-5,7,7,12,14,14-hexa-methyl-1,4,8,11-tetra-azacyclo-tetra-deca-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-methyl-phen-yl)dithio-phos-phates 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 = 957.85

Triclinic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.04

4305 reflections

273 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −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.

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

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

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

[Ni(C16H32N4)](C14H14O2PS2)2	Z = 1
Mr = 957.85	F(000) = 506
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0404P)2 + 0.4007P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
4305 reflections	Δρmax = 0.50 e Å−3
273 parameters	Δρmin = −0.33 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)

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
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)*

	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)

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)