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

Zou, L.-K.; Xie, B.; Feng, J.-S.; Lai, C.

doi:10.1107/S160053681004849X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages m1663-m1664

https://doi.org/10.1107/S160053681004849X

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

Li-Ke Zou,^a ^* Bin Xie,^a Jian-Shen Feng ^a and Chuan Lai ^a

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

(Received 13 November 2010; accepted 21 November 2010; online 27 November 2010)

The title complex, [Ni(C₂₄H₃₂N₄)](C₁₄H₁₄O₂PS₂)₂, comprises a centrosymmetric [Ni(meso-diphenyl[14]dien)]²⁺ dication (meso-diphenyl[14]dien is C-meso-N-meso-5,12-dimethyl-7,14-diphenyl-1,4,8,11-tetraazacyclotetradeca-4,11-diene) and two O,O′-bis(4-methylphenyl) dithiophosphate anions. The Ni^II ion lies on an inversion center and is chelated by a tetraamine macrocycle ligand in a slightly distorted NiN₄ square-planar geometry. Two S atoms from symmetry-related anions are located in pseudo-axial positions with respect to the Ni^II ion, with Ni⋯S distances of 3.1869 (8) Å. In the crystal, bifurcated intermolecular N—H⋯S(S) hydrogen bonds connect cations and pairs of anions into three-component clusters. Weak intermolecular C—H⋯S hydrogen bonds link these clusters into chains along [100].

Related literature

For the synthesis of the tetramine macrocyclic ligand, see: Curtis (2001). For general background to tetramine macrocycles, see: Aoki & Kimura (2002 ); For transition metal complexes with O,O′-dialkyldithiophosphate ligands, see: Drew et al. (1987 ); Liaw et al. (2005 ); Zou et al. (2009 ). For the synthesis and crystal structures of related macrocyclic nickel and copper complexes, see: Feng et al. (2009 ); He et al. (2010 ); Xie et al. (2009 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Ni(C₂₄H₃₂N₄)](C₁₄H₁₄O₂PS₂)₂
M_r = 1053.93
Monoclinic, P 2₁ /n
a = 10.04828 (18) Å
b = 19.6896 (4) Å
c = 13.5112 (3) Å
β = 106.900 (2)°
V = 2557.69 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 150 K
0.22 × 0.18 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.930, T_max = 1
11501 measured reflections
5232 independent reflections
4326 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.085
S = 1.01
5232 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1	0.93	2.87	3.4652 (17)	123
N2—H2⋯S2	0.93	2.71	3.5789 (17)	156
C5—H5B⋯S2ⁱ	0.98	2.87	3.815 (2)	162
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: https://doi.org/10.1107/S160053681004849X/lh5160sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004849X/lh5160Isup2.hkl

checkCIF report

Comment top

The significance of synthetic tetramine macrocycles is most obvious because of their strong chelating ability and analogy to naturally occurring macrocyclic systems, therefore the synthesis and potential use of their transition-metal complexes have been extensively studied (Aoki et al., 2002). At the same time, the transition-metal complexes of O,O'- dialkyldithiophosphate ligands (DDP) have attracted our attention due to their luxuriant variety of coordination bonding characteristics (Drew et al., 1987; Liaw et al., 2005) and potential application as mimetic hydrolases for carboxylic acid esters (Zou et al., 2009). For these reasons, we have recently reported several structures of tetramine macrocyclic transition-metal adducts with O,O'-dialkyldithiophosphate (Feng et al., 2009; Xie et al., 2009; He et al., 2010). Herein, we report the structure of [Ni(meso-diphenyl[14]dien)][S₂P(OC₆H₄Me-4)₂]₂, where meso-diphenyl[14]dien is C-meso-N-meso-5,12-dimethyl-7,14- diphenyl-1,4,8,11-tetraazacyclotetradeca-4,11-diene.

The molecular of the title complex comprises a complex mononuclear [Ni(meso-diphenyl[14]dien)]²⁺ cation and two O,O'-bis(4-methylphenyl) dithiophosphate anions. The Ni^II atom lies on an inversion centre and is chelated by four N atoms from the macrocyclic tetramine meso-diphenyl[14]dien in a slightly distorted NiN₄ square-planar geometry (Fig.1). Two uncoordinated O,O'-bis(4-methylphenyl) dithiophosphate anions occupy pseudo-axial positions with Cu···S distances of 3.1869 (7) Å, forming a octahedral type arrangement. Intermolecular N—H···S and C—H···S hydrogen bonds are present between the anions and the cations. All bond lengths (Allen et al., 1987) and angles in the complex are within normal ranges.

Related literature top

For the synthesis of the tetraamine macrocyclic ligand, see: Curtis (2001). For general background to tetramine macrocycles, see: Aoki et al. (2002); For transition metal complexes with O,O'-dialkyldithiophosphate ligands, see: Drew et al. (1987); Liaw et al. (2005); Zou et al. (2009). For the synthesis and crystal structures of related macrocyclic nickel and copper complexes, see: Feng et al. (2009); He et al. (2010); Xie et al. (2009). For standard bond-length data, see: Allen et al. (1987).

Experimental top

The tetraamine macrocyclic ligand 5,12-Dimethyl-7,14-diphenyl-1,4,8,11- tetraazacyclotetradeca-4,11-diene (diphenyl[14]dien) and [Ni(diphenyl[14]dien)](ClO₄)₂ (a mixture of meso- and rac- isomers) were prepared according to the procedure described by Curtis (2001).

The title complex was prepared by a modified method according to our previous work (Xie et al., 2009). A cellulose thimble containing 0.634 g (1 mmol) of mixed isomers of [Ni(diphenyl[14]dien)](ClO₄)₂ was placed in a Soxhlet apparatus. The isomers were slowly extracted to a solution of 0.767 g (2 mmol) [(C₂H₅)₂NH₂][S₂P(OC₆H₄Me-4)₂] in 70 mL methanol (extraction solvent) and the less soluble meso-isomer of the adduct, [Ni(diphenyl[14]dien)][S₂P(OC₆H₄Me-4)₂]₂, was slowly pricipitated out during the extraction procedure. The whole extraction process lasted about 36 hours and then refluxed for another 4 hours. After cooling to room temperature, the solid was filtered off and washed successively with methanol, acetone and diethyl ether. The crude product was dissolved in hot dimethylformamide and filtered, the filtrate was kept at room temperature and pale-violet block crystals suitable for X-ray diffraction studies were obtained after three months.

Structure description top

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2009); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009); 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. The molecular structure of the title complex, showing the atom-numbering scheme with displacement ellipsoids at 30% probability level. H atoms on N are represented as small spheres of arbitary radii and H atoms on C have been omitted for the sake of clarity. Hydrogen-bonds are shown as dashed lines. [Symmetry code: (i) -x + 1, -y, -z + 1].

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

Crystal data top

[Ni(C₂₄H₃₂N₄)](C₁₄H₁₄O₂PS₂)₂	F(000) = 1108
M_r = 1053.93	D_x = 1.368 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 5452 reflections
a = 10.04828 (18) Å	θ = 3.0–29.2°
b = 19.6896 (4) Å	µ = 0.65 mm⁻¹
c = 13.5112 (3) Å	T = 150 K
β = 106.900 (2)°	Block, pale-violet
V = 2557.69 (9) Å³	0.22 × 0.18 × 0.16 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	5232 independent reflections
Radiation source: fine-focus sealed tube	4326 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 3.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	k = −24→22
T_min = 0.930, T_max = 1.0	l = −16→16
11501 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.033P)² + 1.139P] where P = (F_o² + 2F_c²)/3
5232 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Ni(C₂₄H₃₂N₄)](C₁₄H₁₄O₂PS₂)₂	V = 2557.69 (9) Å³
M_r = 1053.93	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.04828 (18) Å	µ = 0.65 mm⁻¹
b = 19.6896 (4) Å	T = 150 K
c = 13.5112 (3) Å	0.22 × 0.18 × 0.16 mm
β = 106.900 (2)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	5232 independent reflections
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	4326 reflections with I > 2σ(I)
T_min = 0.930, T_max = 1.0	R_int = 0.025
11501 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.01	Δρ_max = 0.39 e Å⁻³
5232 reflections	Δρ_min = −0.28 e Å⁻³
307 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.0000	0.5000	0.01821 (10)
N2	0.65018 (15)	0.05440 (8)	0.58612 (13)	0.0187 (4)
H2	0.6883	0.0785	0.5417	0.022*
N1	0.36007 (16)	0.06810 (8)	0.49274 (12)	0.0194 (4)
C7	0.7393 (2)	0.14121 (10)	0.72455 (16)	0.0231 (4)
C3	0.6128 (2)	0.10500 (10)	0.65498 (16)	0.0230 (4)
H3	0.5655	0.0804	0.7001	0.028*
C12	0.8221 (2)	0.18311 (11)	0.68330 (17)	0.0273 (5)
H12	0.8003	0.1886	0.6105	0.033*
C1	0.37339 (19)	0.12907 (10)	0.52677 (16)	0.0215 (4)
C4	0.22025 (19)	0.04534 (10)	0.42970 (17)	0.0257 (5)
H4A	0.1666	0.0842	0.3917	0.031*
H4B	0.1683	0.0256	0.4748	0.031*
C6	0.7588 (2)	0.00694 (10)	0.64466 (16)	0.0248 (5)
H6A	0.7291	−0.0150	0.7007	0.030*
H6B	0.8467	0.0317	0.6761	0.030*
C2	0.5110 (2)	0.15594 (11)	0.59068 (18)	0.0301 (5)
H2B	0.4934	0.1910	0.6379	0.036*
H2A	0.5562	0.1788	0.5437	0.036*
C5	0.2573 (2)	0.18000 (11)	0.50298 (18)	0.0294 (5)
H5A	0.2449	0.1989	0.4338	0.044*
H5C	0.2801	0.2167	0.5542	0.044*
H5B	0.1711	0.1577	0.5054	0.044*
C11	0.9352 (2)	0.21660 (12)	0.74757 (18)	0.0330 (5)
H11	0.9908	0.2450	0.7187	0.040*
C9	0.8874 (2)	0.16789 (13)	0.89515 (18)	0.0382 (6)
H9	0.9094	0.1626	0.9680	0.046*
C8	0.7738 (2)	0.13401 (12)	0.83067 (17)	0.0310 (5)
H8	0.7190	0.1055	0.8600	0.037*
C10	0.9680 (2)	0.20904 (12)	0.85370 (19)	0.0368 (6)
H10	1.0459	0.2322	0.8977	0.044*
P1	0.73840 (5)	0.08481 (3)	0.33089 (4)	0.02337 (13)
S1	0.54518 (6)	0.10019 (3)	0.32732 (5)	0.03221 (15)
S2	0.88615 (6)	0.11448 (3)	0.45192 (4)	0.03143 (14)
O2	0.75506 (14)	0.11660 (7)	0.22395 (11)	0.0274 (3)
O1	0.77128 (15)	0.00483 (7)	0.31873 (11)	0.0272 (3)
C20	0.8809 (2)	0.11224 (11)	0.19887 (16)	0.0255 (5)
C23	1.1212 (2)	0.10828 (13)	0.13572 (17)	0.0332 (6)
C14	0.5849 (2)	−0.02229 (11)	0.16048 (17)	0.0286 (5)
H14	0.5515	0.0231	0.1527	0.034*
C13	0.6975 (2)	−0.04031 (11)	0.24365 (17)	0.0261 (5)
C25	0.9101 (2)	0.05523 (12)	0.14963 (17)	0.0306 (5)
H25	0.8484	0.0175	0.1366	0.037*
C17	0.6815 (3)	−0.15446 (12)	0.1808 (2)	0.0385 (6)
H17	0.7156	−0.1997	0.1883	0.046*
C21	0.9712 (2)	0.16664 (11)	0.21960 (17)	0.0304 (5)
H21	0.9519	0.2053	0.2552	0.037*
C16	0.5682 (2)	−0.13849 (12)	0.09778 (19)	0.0349 (6)
C15	0.5220 (2)	−0.07171 (12)	0.08889 (18)	0.0314 (5)
H15	0.4450	−0.0594	0.0320	0.038*
C18	0.7466 (2)	−0.10621 (11)	0.25325 (19)	0.0324 (5)
H18	0.8247	−0.1184	0.3094	0.039*
C22	1.0910 (2)	0.16418 (13)	0.18768 (17)	0.0342 (6)
H22	1.1533	0.2016	0.2018	0.041*
C26	1.2453 (2)	0.10744 (16)	0.0941 (2)	0.0518 (8)
H26B	1.2785	0.0607	0.0935	0.078*
H26C	1.3196	0.1355	0.1382	0.078*
H26A	1.2182	0.1256	0.0235	0.078*
C24	1.0306 (2)	0.05370 (13)	0.11934 (17)	0.0341 (5)
H24	1.0516	0.0141	0.0865	0.041*
C19	0.4963 (3)	−0.19066 (14)	0.0184 (2)	0.0526 (8)
H19A	0.4047	−0.2011	0.0265	0.079*
H19C	0.5525	−0.2322	0.0282	0.079*
H19B	0.4851	−0.1726	−0.0512	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01354 (17)	0.01832 (19)	0.0208 (2)	0.00210 (14)	0.00195 (14)	−0.00173 (15)
N2	0.0153 (8)	0.0185 (8)	0.0218 (9)	0.0012 (7)	0.0042 (7)	0.0012 (7)
N1	0.0160 (8)	0.0202 (9)	0.0208 (9)	0.0003 (7)	0.0037 (7)	0.0022 (7)
C7	0.0198 (10)	0.0246 (11)	0.0238 (11)	0.0035 (8)	0.0043 (8)	−0.0058 (9)
C3	0.0199 (10)	0.0281 (11)	0.0219 (11)	−0.0018 (9)	0.0074 (8)	−0.0063 (9)
C12	0.0248 (10)	0.0302 (12)	0.0257 (12)	0.0012 (9)	0.0052 (9)	−0.0035 (10)
C1	0.0192 (10)	0.0217 (11)	0.0238 (11)	0.0028 (8)	0.0068 (8)	0.0009 (9)
C4	0.0142 (9)	0.0213 (11)	0.0369 (13)	0.0017 (8)	−0.0001 (9)	0.0005 (10)
C6	0.0201 (10)	0.0213 (11)	0.0267 (12)	0.0029 (8)	−0.0030 (8)	0.0037 (9)
C2	0.0204 (10)	0.0256 (12)	0.0405 (14)	0.0028 (9)	0.0029 (9)	−0.0102 (10)
C5	0.0230 (10)	0.0204 (11)	0.0416 (14)	0.0046 (9)	0.0044 (9)	−0.0028 (10)
C11	0.0265 (11)	0.0286 (13)	0.0429 (15)	−0.0019 (10)	0.0088 (10)	−0.0077 (11)
C9	0.0380 (13)	0.0442 (15)	0.0259 (13)	0.0053 (11)	−0.0009 (10)	−0.0084 (11)
C8	0.0302 (12)	0.0359 (13)	0.0263 (12)	0.0012 (10)	0.0072 (9)	−0.0027 (10)
C10	0.0262 (11)	0.0359 (13)	0.0399 (15)	0.0000 (10)	−0.0036 (10)	−0.0142 (12)
P1	0.0218 (3)	0.0267 (3)	0.0235 (3)	0.0008 (2)	0.0095 (2)	0.0013 (2)
S1	0.0223 (3)	0.0446 (4)	0.0323 (3)	0.0051 (2)	0.0119 (2)	0.0032 (3)
S2	0.0263 (3)	0.0397 (3)	0.0285 (3)	−0.0055 (2)	0.0084 (2)	−0.0055 (3)
O2	0.0245 (7)	0.0321 (8)	0.0281 (8)	0.0041 (6)	0.0117 (6)	0.0071 (7)
O1	0.0287 (8)	0.0258 (8)	0.0256 (8)	0.0026 (6)	0.0055 (6)	0.0008 (7)
C20	0.0226 (10)	0.0339 (12)	0.0215 (11)	0.0019 (9)	0.0088 (8)	0.0068 (10)
C23	0.0220 (11)	0.0558 (16)	0.0203 (11)	0.0021 (11)	0.0037 (9)	0.0110 (11)
C14	0.0326 (12)	0.0261 (11)	0.0283 (12)	−0.0017 (10)	0.0109 (10)	0.0045 (10)
C13	0.0288 (11)	0.0278 (12)	0.0255 (12)	−0.0030 (9)	0.0138 (9)	0.0012 (10)
C25	0.0308 (12)	0.0367 (13)	0.0259 (12)	−0.0037 (10)	0.0107 (9)	−0.0001 (10)
C17	0.0433 (14)	0.0233 (12)	0.0577 (17)	−0.0031 (11)	0.0284 (13)	0.0003 (12)
C21	0.0329 (12)	0.0280 (12)	0.0303 (13)	0.0003 (10)	0.0091 (10)	0.0058 (10)
C16	0.0395 (13)	0.0307 (13)	0.0425 (15)	−0.0141 (11)	0.0247 (12)	−0.0050 (11)
C15	0.0316 (12)	0.0356 (13)	0.0286 (12)	−0.0094 (10)	0.0113 (10)	0.0009 (11)
C18	0.0335 (12)	0.0282 (12)	0.0390 (14)	0.0019 (10)	0.0160 (10)	0.0043 (11)
C22	0.0282 (11)	0.0421 (14)	0.0301 (13)	−0.0079 (11)	0.0052 (10)	0.0121 (11)
C26	0.0261 (12)	0.092 (2)	0.0389 (15)	0.0024 (14)	0.0126 (11)	0.0119 (15)
C24	0.0343 (12)	0.0459 (15)	0.0236 (12)	0.0058 (11)	0.0107 (10)	−0.0011 (11)
C19	0.0566 (17)	0.0418 (16)	0.066 (2)	−0.0235 (13)	0.0277 (15)	−0.0154 (14)

Geometric parameters (Å, º) top

Ni1—N2	1.9385 (15)	C10—H10	0.9500
Ni1—N2ⁱ	1.9385 (15)	P1—S1	1.9517 (7)
Ni1—N1	1.9247 (16)	P1—S2	1.9514 (8)
Ni1—N1ⁱ	1.9247 (16)	P1—O2	1.6273 (15)
N2—H2	0.9300	P1—O1	1.6271 (15)
N2—C3	1.484 (2)	O2—C20	1.403 (2)
N2—C6	1.479 (2)	O1—C13	1.390 (3)
N1—C1	1.279 (3)	C20—C25	1.379 (3)
N1—C4	1.485 (2)	C20—C21	1.379 (3)
C7—C3	1.521 (3)	C23—C22	1.386 (3)
C7—C12	1.397 (3)	C23—C26	1.510 (3)
C7—C8	1.381 (3)	C23—C24	1.384 (3)
C3—H3	1.0000	C14—H14	0.9500
C3—C2	1.513 (3)	C14—C13	1.389 (3)
C12—H12	0.9500	C14—C15	1.388 (3)
C12—C11	1.381 (3)	C13—C18	1.381 (3)
C1—C2	1.498 (3)	C25—H25	0.9500
C1—C5	1.500 (3)	C25—C24	1.387 (3)
C4—H4A	0.9900	C17—H17	0.9500
C4—H4B	0.9900	C17—C16	1.382 (3)
C4—C6ⁱ	1.495 (3)	C17—C18	1.385 (3)
C6—C4ⁱ	1.495 (3)	C21—H21	0.9500
C6—H6A	0.9900	C21—C22	1.393 (3)
C6—H6B	0.9900	C16—C15	1.388 (3)
C2—H2B	0.9900	C16—C19	1.509 (3)
C2—H2A	0.9900	C15—H15	0.9500
C5—H5A	0.9800	C18—H18	0.9500
C5—H5C	0.9800	C22—H22	0.9500
C5—H5B	0.9800	C26—H26B	0.9800
C11—H11	0.9500	C26—H26C	0.9800
C11—C10	1.383 (3)	C26—H26A	0.9800
C9—H9	0.9500	C24—H24	0.9500
C9—C8	1.389 (3)	C19—H19A	0.9800
C9—C10	1.375 (3)	C19—H19C	0.9800
C8—H8	0.9500	C19—H19B	0.9800

Ni1—N2—H2	106.8	C8—C7—C12	118.43 (19)
N2ⁱ—Ni1—N2	180	C8—C9—H9	119.9
N2—C3—C7	112.54 (15)	C10—C11—H11	119.8
N2—C3—H3	108.0	C10—C9—H9	119.9
N2—C3—C2	109.70 (16)	C10—C9—C8	120.1 (2)
N2—C6—C4ⁱ	107.56 (16)	S2—P1—S1	118.90 (4)
N2—C6—H6A	110.2	O2—P1—S1	106.07 (6)
N2—C6—H6B	110.2	O2—P1—S2	112.29 (6)
N1—Ni1—N2	94.32 (7)	O1—P1—S1	112.17 (6)
N1—Ni1—N2ⁱ	85.68 (7)	O1—P1—S2	104.30 (6)
N1ⁱ—Ni1—N2	85.68 (7)	O1—P1—O2	101.90 (8)
N1ⁱ—Ni1—N2ⁱ	94.32 (7)	C20—O2—P1	121.56 (13)
N1ⁱ—Ni1—N1	180	C20—C25—H25	120.4
N1—C1—C2	121.44 (17)	C20—C25—C24	119.1 (2)
N1—C1—C5	123.84 (18)	C20—C21—H21	120.4
N1—C4—H4A	110.2	C20—C21—C22	119.2 (2)
N1—C4—H4B	110.2	C23—C22—C21	121.4 (2)
N1—C4—C6ⁱ	107.38 (16)	C23—C22—H22	119.3
C7—C3—H3	108.0	C23—C26—H26B	109.5
C7—C12—H12	119.7	C23—C26—H26C	109.5
C7—C8—C9	121.0 (2)	C23—C26—H26A	109.5
C7—C8—H8	119.5	C23—C24—C25	121.8 (2)
C3—N2—Ni1	116.89 (11)	C23—C24—H24	119.1
C3—N2—H2	106.8	C14—C13—O1	124.28 (19)
C3—C2—H2B	108.1	C14—C15—H15	119.0
C3—C2—H2A	108.1	C13—O1—P1	127.73 (13)
C12—C7—C3	121.19 (18)	C13—C14—H14	120.5
C12—C11—H11	119.8	C13—C18—C17	119.7 (2)
C12—C11—C10	120.3 (2)	C13—C18—H18	120.1
C1—N1—Ni1	129.59 (14)	C25—C20—O2	119.94 (19)
C1—N1—C4	118.19 (16)	C25—C24—H24	119.1
C1—C2—C3	116.97 (17)	C17—C16—C15	117.5 (2)
C1—C2—H2B	108.1	C17—C16—C19	122.2 (2)
C1—C2—H2A	108.1	C17—C18—H18	120.1
C1—C5—H5A	109.5	C21—C20—O2	119.30 (19)
C1—C5—H5C	109.5	C21—C20—C25	120.69 (19)
C1—C5—H5B	109.5	C21—C22—H22	119.3
C4—N1—Ni1	111.99 (12)	C16—C17—H17	119.1
C4ⁱ—C6—H6A	110.2	C16—C17—C18	121.8 (2)
C4ⁱ—C6—H6B	110.2	C16—C15—C14	122.1 (2)
H4A—C4—H4B	108.5	C16—C15—H15	119.0
C6—N2—Ni1	107.25 (12)	C16—C19—H19A	109.5
C6—N2—H2	106.8	C16—C19—H19C	109.5
C6—N2—C3	111.77 (15)	C16—C19—H19B	109.5
C6ⁱ—C4—H4A	110.2	C15—C14—H14	120.5
C6ⁱ—C4—H4B	110.2	C15—C14—C13	118.9 (2)
H6A—C6—H6B	108.5	C15—C16—C19	120.3 (2)
C2—C3—C7	110.38 (16)	C18—C13—O1	115.63 (19)
C2—C3—H3	108.0	C18—C13—C14	120.0 (2)
C2—C1—C5	114.66 (17)	C18—C17—H17	119.1
H2B—C2—H2A	107.3	C22—C23—C26	121.6 (2)
H5A—C5—H5C	109.5	C22—C21—H21	120.4
H5A—C5—H5B	109.5	H26B—C26—H26C	109.5
H5C—C5—H5B	109.5	H26B—C26—H26A	109.5
C11—C12—C7	120.5 (2)	H26C—C26—H26A	109.5
C11—C12—H12	119.7	C24—C23—C22	117.8 (2)
C11—C10—H10	120.2	C24—C23—C26	120.5 (2)
C9—C8—H8	119.5	C24—C25—H25	120.4
C9—C10—C11	119.7 (2)	H19A—C19—H19C	109.5
C9—C10—H10	120.2	H19A—C19—H19B	109.5
C8—C7—C3	120.38 (19)	H19C—C19—H19B	109.5

Ni1—N2—C3—C7	175.86 (13)	C8—C7—C12—C11	−0.2 (3)
Ni1—N2—C3—C2	−60.84 (19)	C8—C9—C10—C11	0.1 (4)
Ni1—N2—C6—C4ⁱ	45.69 (18)	C10—C9—C8—C7	−0.4 (3)
Ni1—N1—C1—C2	−6.0 (3)	P1—O2—C20—C25	85.7 (2)
Ni1—N1—C1—C5	171.17 (15)	P1—O2—C20—C21	−97.2 (2)
Ni1—N1—C4—C6ⁱ	−25.2 (2)	P1—O1—C13—C14	4.3 (3)
N2ⁱ—Ni1—N1—C1	−174.21 (19)	P1—O1—C13—C18	−178.36 (15)
N2—Ni1—N1—C1	5.79 (19)	S1—P1—O2—C20	−177.67 (14)
N2—Ni1—N1—C4	180.00 (13)	S1—P1—O1—C13	50.57 (17)
N2ⁱ—Ni1—N1—C4	0.00 (13)	S2—P1—O2—C20	50.91 (16)
N2—C3—C2—C1	62.2 (2)	S2—P1—O1—C13	−179.45 (15)
N1—Ni1—N2—C3	28.14 (14)	O2—P1—O1—C13	−62.47 (17)
N1ⁱ—Ni1—N2—C3	−151.86 (14)	O2—C20—C25—C24	175.78 (19)
N1—Ni1—N2—C6	154.50 (13)	O2—C20—C21—C22	−175.25 (18)
N1ⁱ—Ni1—N2—C6	−25.50 (13)	O1—P1—O2—C20	−60.14 (16)
N1—C1—C2—C3	−28.3 (3)	O1—C13—C18—C17	−178.68 (19)
C7—C3—C2—C1	−173.27 (18)	C20—C25—C24—C23	−1.1 (3)
C7—C12—C11—C10	0.0 (3)	C20—C21—C22—C23	−0.1 (3)
C3—N2—C6—C4ⁱ	175.03 (16)	C14—C13—C18—C17	−1.2 (3)
C3—C7—C12—C11	178.85 (18)	C13—C14—C15—C16	0.0 (3)
C3—C7—C8—C9	−178.67 (19)	C25—C20—C21—C22	1.7 (3)
C12—C7—C3—N2	64.4 (2)	C17—C16—C15—C14	−0.7 (3)
C12—C7—C3—C2	−58.5 (2)	C21—C20—C25—C24	−1.2 (3)
C12—C7—C8—C9	0.4 (3)	C16—C17—C18—C13	0.4 (3)
C12—C11—C10—C9	0.1 (3)	C15—C14—C13—O1	178.26 (19)
C1—N1—C4—C6ⁱ	149.72 (18)	C15—C14—C13—C18	1.0 (3)
C4—N1—C1—C2	−179.86 (19)	C18—C17—C16—C15	0.5 (3)
C4—N1—C1—C5	−2.7 (3)	C18—C17—C16—C19	−180.0 (2)
C6—N2—C3—C7	51.8 (2)	C22—C23—C24—C25	2.6 (3)
C6—N2—C3—C2	175.07 (16)	C26—C23—C22—C21	175.4 (2)
C5—C1—C2—C3	154.36 (19)	C26—C23—C24—C25	−174.9 (2)
C8—C7—C3—N2	−116.5 (2)	C24—C23—C22—C21	−2.1 (3)
C8—C7—C3—C2	120.6 (2)	C19—C16—C15—C14	179.8 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1	0.93	2.87	3.4652 (17)	123
N2—H2···S2	0.93	2.71	3.5789 (17)	156
C5—H5B···S2ⁱⁱ	0.98	2.87	3.815 (2)	162

Symmetry code: (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Ni(C₂₄H₃₂N₄)](C₁₄H₁₄O₂PS₂)₂
M_r	1053.93
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	10.04828 (18), 19.6896 (4), 13.5112 (3)
β (°)	106.900 (2)
V (Å³)	2557.69 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.22 × 0.18 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos
Absorption correction	Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)
T_min, T_max	0.930, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	11501, 5232, 4326
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.085, 1.01
No. of reflections	5232
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.28

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1	0.93	2.87	3.4652 (17)	123.3
N2—H2···S2	0.93	2.71	3.5789 (17)	156.4
C5—H5B···S2ⁱ	0.98	2.87	3.815 (2)	162

Symmetry code: (i) x−1, y, z.

Acknowledgements

This work was supported by the Education Committee of Sichuan Province (No. 09ZA057), the Science and Technology Office of Zigong City (Nos. 08X01 and 10X05) and the Committee of Science and Technology of Sichuan Province (No. 2010GZ0130).

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. CSD CrossRef Web of Science Google Scholar
Aoki, S. & Kimura, E. (2002). Rev. Mol. Biotechnol. 90, 129–155. CrossRef CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 66| Part 12| December 2010| Pages m1663-m1664

https://doi.org/10.1107/S160053681004849X

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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