(1,2,3,4-Tetra­hydro­isoquinoline-2-carbo­dithio­ato-κ2S,S′)(thio­cyanato-κN)(tri­phenyl­phosphane)nickel(II)

Valarmathi, P.; Thirumaran, S.; Selvanayagam, S.

doi:10.1107/S1600536811050550

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1882

https://doi.org/10.1107/S1600536811050550

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(1,2,3,4-Tetrahydroisoquinoline-2-carbodithioato-κ²S,S′)(thiocyanato-κN)(triphenylphosphane)nickel(II)

P. Valarmathi,^a S. Thirumaran ^a and S. Selvanayagam ^b ^*

^aDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, India, and ^bDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India
^*Correspondence e-mail: s_selvanayagam@rediffmail.com

(Received 22 November 2011; accepted 24 November 2011; online 30 November 2011)

The Ni^II atom in the mononuclear title compound, [Ni(C₁₀H₁₀NS₂)(NCS)(C₁₈H₁₅P)], exists within a S₂PN donor set that defines a distorted square-planar geometry. A significant asymmetry in the Ni—S bond lengths support the less effective trans effect of SCN⁻ over PPh₃.

Related literature

For general background to dithiocarbamates and their biological activity, see: Gunay et al. (1999 ); Hogarth (2005 ); Ozkirimli et al. (2005 ). Nickel complexes of phosphine ligands have been studied for their anticancer activity, see: Jarret et al. (1993 ). Nickel(II) dithiocarbamates can react with Lewis bases such as phosphines as well as hard bases such as nitrogenous ligands, see: Srinivasan et al. (2009 ); Travnicek et al. (2008 ). For the preparation of the title compound, see: Valarmathi et al. (2011 ).

Experimental

Crystal data

[Ni(C₁₀H₁₀NS₂)(NCS)(C₁₈H₁₅P)]
M_r = 587.37
Monoclinic, P 2₁ /n
a = 13.7981 (4) Å
b = 13.1429 (4) Å
c = 14.9447 (4) Å
β = 91.693 (2)°
V = 2708.99 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 292 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 1999 ) T_min = 0.783, T_max = 0.861
33862 measured reflections
7287 independent reflections
5132 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.123
S = 1.03
7287 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected bond lengths (Å)

N1—Ni1	1.867 (2)
P1—Ni1	2.1874 (6)
S1—Ni1	2.218 (1)
S2—Ni1	2.162 (1)

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811050550/bt5724sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050550/bt5724Isup2.hkl

checkCIF report

Comment top

Dithiocarbamates are versatile ligands which have been shown to bind to all transition elements supporting a wide range of oxidation state (Hogarth, 2005). They have been shown to posses a broad spectrum of biological activities such as fungicidal (Ozkirimli et al., 2005) and bactericidal (Gunay et al., 1999). Nickel complexes of phosphine ligands have been studied for their anticancer activity (Jarret et al., 1993). Nickel(II) dithiocarbamates are borderline acceptors and they can react with Lewis bases such as phosphines as well as hard bases such as nitrogenous ligands (Srinivasan et al., 2009; Travnicek et al., 2008). In view of these importance we have undertaken the crystal structure determination of the title compound, and the results are presented here.

The X-ray study confirmed the molecular structure and atomic connectivity for (I), as illustrated in Fig. 1.

The structure consists of distorted square planar metal coordination with NiS₂PN chromophore. Deviation of the plane from a perfect square is caused by the small bite angle subtended by the sulfur atoms of the chelating dithiocarbamate at the nickel atom. The Ni—S bond distances [2.218 (1) and 2.162 (1) Å, respectively] are significantly different, due to the different trans influences exerted by phosphine and NCS^-. PPh₃ being a good π-acceptor has a greater trans influence and hence the Ni—S bond trans to P is longer than the one trans to NCS anion.

The shortening of Ni—P distance is due the strong back bonding in nickel atom. The C—P—C angles deviate appreciably from the normal tetrahedral angle due to the crowding of the phenyl rings. The short Ni—N distance, 1.867 (2) Å, shows the effective bonding between the nickel atom and NCS^-. The Ni—N—C angle 170.9 (2)° indicates deviation from the linearity and is due to steric compulsions of the bulky PPh₃ group.

The C—S bond lengths are 1.707 (3) and 1.717 (3) Å which are shorter than the typical single bond value of 1.81 Å and longer than C=S distance of 1.69 Å, indicating partial double bond character. The short thioureide C—N distance, 1.315 (3) Å indicates that the π-electron density is delocalised over the S₂CN moiety and that this bond has partial double bond character.

In addition to the van der Waals interactions, the molecular structure is influenced only by intramolecular C—H···S hydrogen bonds involving sulphur atoms S1 and S2. (Fig. 2 and Table 1).

Related literature top

For general background to dithiocarbamates and their biological activity, see: Gunay et al. (1999); Hogarth (2005); Ozkirimli et al. (2005). Nickel complexes of phosphine ligands have been studied for their anticancer activity, see: Jarret et al. (1993). Nickel(II) dithiocarbamates can react with Lewis bases such as phosphines as well as hard bases such as nitrogenous ligands, see: Srinivasan et al. (2009); Travnicek et al. (2008). For the preparation of the title compound, see: Valarmathi et al. (2011).

Experimental top

Compound (I) was prepared according to the literature procedure (Valarmathi et al., 2011). Single crystals of (I) were obtained by slow evaporation of dichloromethane and ethanol (2:1) solution of (I) at room temperature.

Structure description top

The X-ray study confirmed the molecular structure and atomic connectivity for (I), as illustrated in Fig. 1.

In addition to the van der Waals interactions, the molecular structure is influenced only by intramolecular C—H···S hydrogen bonds involving sulphur atoms S1 and S2. (Fig. 2 and Table 1).

For general background to dithiocarbamates and their biological activity, see: Gunay et al. (1999); Hogarth (2005); Ozkirimli et al. (2005). Nickel complexes of phosphine ligands have been studied for their anticancer activity, see: Jarret et al. (1993). Nickel(II) dithiocarbamates can react with Lewis bases such as phosphines as well as hard bases such as nitrogenous ligands, see: Srinivasan et al. (2009); Travnicek et al. (2008). For the preparation of the title compound, see: Valarmathi et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)'; software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level
	Fig. 2. Molecular packing of the title compound, viewed along the b axis; H-bonds are shown as dashed lines. For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted

(1,2,3,4-Tetrahydroisoquinoline-2-carbodithioato- κ²S,S')(thiocyanato-κN)(triphenylphosphane)nickel(II) top

Crystal data top

[Ni(C₁₀H₁₀NS₂)(NCS)(C₁₈H₁₅P)]	F(000) = 1216
M_r = 587.37	D_x = 1.440 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8723 reflections
a = 13.7981 (4) Å	θ = 2.5–26.3°
b = 13.1429 (4) Å	µ = 1.03 mm⁻¹
c = 14.9447 (4) Å	T = 292 K
β = 91.693 (2)°	Block, pale-yellow
V = 2708.99 (13) Å³	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker KAPPA APEXII CCD diffractometer	7287 independent reflections
Radiation source: fine-focus sealed tube	5132 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω and φ scan	θ_max = 29.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker 1999)	h = −18→17
T_min = 0.783, T_max = 0.861	k = −11→17
33862 measured reflections	l = −20→20

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0574P)² + 1.2033P] where P = (F_o² + 2F_c²)/3
7287 reflections	(Δ/σ)_max = 0.001
325 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Ni(C₁₀H₁₀NS₂)(NCS)(C₁₈H₁₅P)]	V = 2708.99 (13) Å³
M_r = 587.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.7981 (4) Å	µ = 1.03 mm⁻¹
b = 13.1429 (4) Å	T = 292 K
c = 14.9447 (4) Å	0.25 × 0.20 × 0.15 mm
β = 91.693 (2)°

Data collection top

Bruker KAPPA APEXII CCD diffractometer	7287 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 1999)	5132 reflections with I > 2σ(I)
T_min = 0.783, T_max = 0.861	R_int = 0.035
33862 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.03	Δρ_max = 0.55 e Å⁻³
7287 reflections	Δρ_min = −0.30 e Å⁻³
325 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
C1	0.67037 (18)	0.52602 (19)	0.77990 (18)	0.0474 (6)
C2	0.70333 (19)	0.61484 (19)	0.43746 (18)	0.0486 (6)
C3	0.5892 (3)	0.5795 (3)	0.3133 (2)	0.0739 (9)
H3A	0.5591	0.6295	0.2737	0.089*
H3B	0.5448	0.5654	0.3609	0.089*
C4	0.6072 (3)	0.4837 (3)	0.2622 (3)	0.0850 (11)
H4A	0.6227	0.4289	0.3036	0.102*
H4B	0.5490	0.4650	0.2280	0.102*
C5	0.6874 (2)	0.4983 (3)	0.2015 (2)	0.0694 (9)
C6	0.6980 (4)	0.4273 (3)	0.1283 (3)	0.0919 (12)
H6	0.6541	0.3740	0.1207	0.110*
C7	0.7711 (4)	0.4377 (4)	0.0712 (3)	0.0969 (13)
H7	0.7773	0.3920	0.0242	0.116*
C8	0.8378 (3)	0.5175 (4)	0.0825 (3)	0.0950 (13)
H8	0.8875	0.5249	0.0424	0.114*
C9	0.8305 (3)	0.5845 (3)	0.1519 (2)	0.0777 (10)
H9	0.8755	0.6365	0.1602	0.093*
C10	0.7549 (2)	0.5731 (2)	0.20951 (19)	0.0592 (7)
C11	0.7468 (3)	0.6536 (3)	0.2850 (2)	0.0742 (9)
H11A	0.8102	0.6644	0.3131	0.089*
H11B	0.7250	0.7176	0.2593	0.089*
C12	1.00159 (18)	0.65116 (18)	0.63240 (16)	0.0424 (5)
C13	0.9915 (2)	0.7503 (2)	0.60153 (18)	0.0518 (6)
H13	0.9327	0.7838	0.6071	0.062*
C14	1.0679 (2)	0.7995 (2)	0.5627 (2)	0.0631 (8)
H14	1.0608	0.8663	0.5430	0.076*
C15	1.1541 (2)	0.7499 (3)	0.5532 (2)	0.0698 (9)
H15	1.2054	0.7827	0.5263	0.084*
C16	1.1653 (2)	0.6520 (3)	0.5833 (2)	0.0707 (9)
H16	1.2240	0.6185	0.5765	0.085*
C17	1.0890 (2)	0.6025 (2)	0.6240 (2)	0.0580 (7)
H17	1.0972	0.5366	0.6455	0.070*
C18	0.92192 (16)	0.46836 (17)	0.71702 (16)	0.0401 (5)
C19	0.9523 (2)	0.3997 (2)	0.65279 (19)	0.0526 (6)
H19	0.9652	0.4223	0.5954	0.063*
C20	0.9633 (2)	0.2978 (2)	0.6743 (2)	0.0663 (8)
H20	0.9850	0.2525	0.6315	0.080*
C21	0.9426 (2)	0.2629 (2)	0.7583 (2)	0.0632 (8)
H21	0.9508	0.1945	0.7725	0.076*
C22	0.9100 (2)	0.3294 (2)	0.8207 (2)	0.0587 (7)
H22	0.8946	0.3056	0.8771	0.070*
C23	0.89970 (19)	0.4318 (2)	0.80110 (18)	0.0492 (6)
H23	0.8778	0.4762	0.8445	0.059*
C24	0.89695 (17)	0.67053 (17)	0.79026 (15)	0.0404 (5)
C25	0.9742 (2)	0.6615 (2)	0.85052 (18)	0.0534 (6)
H25	1.0243	0.6165	0.8390	0.064*
C26	0.9775 (2)	0.7188 (2)	0.9275 (2)	0.0671 (8)
H26	1.0290	0.7114	0.9685	0.080*
C27	0.9048 (3)	0.7866 (2)	0.9437 (2)	0.0658 (8)
H27	0.9073	0.8254	0.9958	0.079*
C28	0.8290 (2)	0.7977 (2)	0.8845 (2)	0.0619 (7)
H28	0.7803	0.8445	0.8958	0.074*
C29	0.82414 (19)	0.7394 (2)	0.80687 (18)	0.0503 (6)
H29	0.7721	0.7468	0.7664	0.060*
N1	0.69817 (16)	0.54668 (18)	0.71207 (15)	0.0518 (5)
N2	0.67965 (18)	0.6210 (2)	0.35176 (15)	0.0612 (6)
P1	0.89629 (4)	0.59881 (4)	0.68659 (4)	0.03763 (14)
S1	0.63111 (5)	0.56870 (6)	0.51886 (5)	0.05756 (19)
S2	0.81349 (5)	0.64882 (6)	0.48486 (4)	0.05379 (18)
S3	0.63080 (8)	0.50024 (8)	0.87781 (6)	0.0838 (3)
Ni1	0.75893 (2)	0.59313 (2)	0.60984 (2)	0.04025 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0428 (14)	0.0467 (13)	0.0524 (16)	−0.0003 (10)	−0.0034 (11)	0.0053 (11)
C2	0.0488 (15)	0.0510 (14)	0.0455 (14)	0.0054 (11)	−0.0073 (11)	0.0023 (11)
C3	0.068 (2)	0.098 (3)	0.0535 (18)	0.0035 (17)	−0.0239 (16)	−0.0040 (16)
C4	0.069 (2)	0.098 (3)	0.086 (3)	−0.0164 (19)	−0.0205 (19)	−0.003 (2)
C5	0.067 (2)	0.078 (2)	0.0623 (19)	−0.0082 (16)	−0.0242 (16)	0.0088 (16)
C6	0.109 (3)	0.081 (2)	0.084 (3)	0.013 (2)	−0.023 (2)	−0.011 (2)
C7	0.106 (3)	0.111 (3)	0.072 (3)	0.034 (3)	−0.020 (2)	−0.023 (2)
C8	0.091 (3)	0.121 (3)	0.073 (2)	0.033 (3)	−0.014 (2)	−0.006 (2)
C9	0.070 (2)	0.100 (3)	0.063 (2)	0.0029 (18)	−0.0101 (17)	0.0145 (18)
C10	0.0552 (17)	0.0711 (18)	0.0505 (16)	0.0061 (13)	−0.0122 (13)	0.0131 (13)
C11	0.087 (2)	0.088 (2)	0.0470 (17)	−0.0120 (18)	−0.0133 (16)	0.0092 (15)
C12	0.0427 (13)	0.0472 (13)	0.0371 (12)	−0.0033 (10)	−0.0012 (10)	−0.0015 (10)
C13	0.0558 (16)	0.0490 (14)	0.0506 (15)	−0.0033 (12)	0.0039 (12)	0.0004 (11)
C14	0.083 (2)	0.0525 (15)	0.0543 (17)	−0.0181 (15)	0.0068 (15)	−0.0016 (13)
C15	0.067 (2)	0.082 (2)	0.0611 (19)	−0.0297 (17)	0.0171 (15)	−0.0127 (16)
C16	0.0481 (17)	0.083 (2)	0.081 (2)	−0.0028 (15)	0.0127 (15)	−0.0028 (18)
C17	0.0484 (16)	0.0613 (16)	0.0645 (18)	0.0008 (12)	0.0058 (13)	0.0031 (13)
C18	0.0359 (12)	0.0424 (12)	0.0416 (12)	0.0001 (9)	−0.0062 (9)	−0.0004 (10)
C19	0.0547 (16)	0.0523 (15)	0.0507 (15)	0.0004 (12)	−0.0032 (12)	−0.0057 (12)
C20	0.0629 (19)	0.0477 (15)	0.088 (2)	0.0046 (13)	−0.0062 (16)	−0.0211 (15)
C21	0.0542 (17)	0.0381 (13)	0.096 (2)	−0.0036 (11)	−0.0123 (16)	0.0037 (15)
C22	0.0560 (17)	0.0531 (15)	0.0664 (18)	−0.0091 (12)	−0.0106 (14)	0.0164 (14)
C23	0.0524 (15)	0.0490 (13)	0.0458 (14)	−0.0008 (11)	−0.0034 (11)	0.0031 (11)
C24	0.0448 (13)	0.0396 (11)	0.0369 (12)	0.0000 (9)	0.0003 (10)	0.0002 (9)
C25	0.0569 (16)	0.0524 (14)	0.0499 (15)	0.0060 (12)	−0.0120 (12)	−0.0062 (12)
C26	0.079 (2)	0.0700 (19)	0.0515 (17)	−0.0049 (16)	−0.0184 (15)	−0.0068 (14)
C27	0.089 (2)	0.0596 (17)	0.0493 (16)	−0.0127 (16)	0.0071 (16)	−0.0168 (14)
C28	0.0659 (19)	0.0561 (16)	0.0646 (18)	0.0009 (13)	0.0178 (15)	−0.0133 (14)
C29	0.0476 (15)	0.0514 (14)	0.0519 (15)	0.0038 (11)	0.0013 (12)	−0.0030 (11)
N1	0.0451 (12)	0.0603 (13)	0.0498 (13)	0.0018 (10)	−0.0036 (10)	0.0028 (11)
N2	0.0602 (15)	0.0798 (16)	0.0428 (13)	0.0006 (12)	−0.0109 (11)	0.0018 (11)
P1	0.0381 (3)	0.0410 (3)	0.0336 (3)	0.0027 (2)	−0.0021 (2)	0.0014 (2)
S1	0.0445 (4)	0.0752 (5)	0.0522 (4)	−0.0037 (3)	−0.0108 (3)	0.0107 (3)
S2	0.0529 (4)	0.0690 (4)	0.0390 (3)	−0.0097 (3)	−0.0059 (3)	0.0059 (3)
S3	0.1015 (7)	0.0936 (7)	0.0572 (5)	−0.0079 (5)	0.0185 (5)	0.0166 (4)
Ni1	0.03948 (18)	0.04412 (17)	0.03685 (17)	0.00331 (12)	−0.00393 (12)	0.00315 (12)

Geometric parameters (Å, º) top

C1—N1	1.128 (3)	C15—C16	1.370 (5)
C1—S3	1.613 (3)	C15—H15	0.9300
C2—N2	1.315 (3)	C16—C17	1.392 (4)
C2—S1	1.707 (3)	C16—H16	0.9300
C2—S2	1.717 (3)	C17—H17	0.9300
C3—N2	1.464 (4)	C18—C23	1.388 (3)
C3—C4	1.497 (5)	C18—C19	1.391 (3)
C3—H3A	0.9700	C18—P1	1.806 (2)
C3—H3B	0.9700	C19—C20	1.385 (4)
C4—C5	1.464 (5)	C19—H19	0.9300
C4—H4A	0.9700	C20—C21	1.374 (5)
C4—H4B	0.9700	C20—H20	0.9300
C5—C10	1.357 (4)	C21—C22	1.364 (4)
C5—C6	1.449 (5)	C21—H21	0.9300
C6—C7	1.347 (6)	C22—C23	1.383 (4)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.402 (6)	C23—H23	0.9300
C7—H7	0.9300	C24—C25	1.380 (3)
C8—C9	1.366 (5)	C24—C29	1.381 (3)
C8—H8	0.9300	C24—P1	1.813 (2)
C9—C10	1.380 (5)	C25—C26	1.375 (4)
C9—H9	0.9300	C25—H25	0.9300
C10—C11	1.553 (5)	C26—C27	1.368 (5)
C11—N2	1.447 (4)	C26—H26	0.9300
C11—H11A	0.9700	C27—C28	1.358 (4)
C11—H11B	0.9700	C27—H27	0.9300
C12—C17	1.374 (4)	C28—C29	1.390 (4)
C12—C13	1.387 (4)	C28—H28	0.9300
C12—P1	1.819 (2)	C29—H29	0.9300
C13—C14	1.380 (4)	N1—Ni1	1.867 (2)
C13—H13	0.9300	P1—Ni1	2.1874 (6)
C14—C15	1.367 (5)	S1—Ni1	2.218 (1)
C14—H14	0.9300	S2—Ni1	2.162 (1)

N1—C1—S3	178.2 (3)	C12—C17—H17	120.0
N2—C2—S1	125.6 (2)	C16—C17—H17	120.0
N2—C2—S2	125.3 (2)	C23—C18—C19	118.6 (2)
S1—C2—S2	109.07 (14)	C23—C18—P1	120.66 (19)
N2—C3—C4	111.2 (3)	C19—C18—P1	120.16 (19)
N2—C3—H3A	109.4	C20—C19—C18	120.0 (3)
C4—C3—H3A	109.4	C20—C19—H19	120.0
N2—C3—H3B	109.4	C18—C19—H19	120.0
C4—C3—H3B	109.4	C21—C20—C19	120.7 (3)
H3A—C3—H3B	108.0	C21—C20—H20	119.6
C5—C4—C3	110.2 (3)	C19—C20—H20	119.6
C5—C4—H4A	109.6	C22—C21—C20	119.5 (3)
C3—C4—H4A	109.6	C22—C21—H21	120.3
C5—C4—H4B	109.6	C20—C21—H21	120.3
C3—C4—H4B	109.6	C21—C22—C23	120.9 (3)
H4A—C4—H4B	108.1	C21—C22—H22	119.6
C10—C5—C6	116.6 (4)	C23—C22—H22	119.6
C10—C5—C4	124.8 (3)	C22—C23—C18	120.3 (3)
C6—C5—C4	118.6 (3)	C22—C23—H23	119.9
C7—C6—C5	120.5 (4)	C18—C23—H23	119.9
C7—C6—H6	119.8	C25—C24—C29	119.4 (2)
C5—C6—H6	119.8	C25—C24—P1	119.81 (19)
C6—C7—C8	120.0 (4)	C29—C24—P1	120.62 (19)
C6—C7—H7	120.0	C26—C25—C24	120.3 (3)
C8—C7—H7	120.0	C26—C25—H25	119.8
C9—C8—C7	120.7 (4)	C24—C25—H25	119.8
C9—C8—H8	119.6	C27—C26—C25	119.9 (3)
C7—C8—H8	119.6	C27—C26—H26	120.0
C8—C9—C10	118.5 (4)	C25—C26—H26	120.0
C8—C9—H9	120.8	C28—C27—C26	120.6 (3)
C10—C9—H9	120.8	C28—C27—H27	119.7
C5—C10—C9	123.6 (3)	C26—C27—H27	119.7
C5—C10—C11	119.6 (3)	C27—C28—C29	120.1 (3)
C9—C10—C11	116.8 (3)	C27—C28—H28	119.9
N2—C11—C10	111.1 (3)	C29—C28—H28	119.9
N2—C11—H11A	109.4	C24—C29—C28	119.6 (3)
C10—C11—H11A	109.4	C24—C29—H29	120.2
N2—C11—H11B	109.4	C28—C29—H29	120.2
C10—C11—H11B	109.4	C1—N1—Ni1	170.9 (2)
H11A—C11—H11B	108.0	C2—N2—C11	123.0 (3)
C17—C12—C13	119.1 (2)	C2—N2—C3	122.9 (3)
C17—C12—P1	125.4 (2)	C11—N2—C3	113.3 (2)
C13—C12—P1	115.43 (19)	C18—P1—C24	106.40 (11)
C14—C13—C12	120.6 (3)	C18—P1—C12	108.54 (11)
C14—C13—H13	119.7	C24—P1—C12	101.53 (11)
C12—C13—H13	119.7	C18—P1—Ni1	105.06 (8)
C15—C14—C13	119.9 (3)	C24—P1—Ni1	116.63 (8)
C15—C14—H14	120.1	C12—P1—Ni1	118.07 (8)
C13—C14—H14	120.1	C2—S1—Ni1	85.13 (9)
C14—C15—C16	120.2 (3)	C2—S2—Ni1	86.67 (9)
C14—C15—H15	119.9	N1—Ni1—S2	173.69 (7)
C16—C15—H15	119.9	N1—Ni1—P1	89.15 (7)
C15—C16—C17	120.2 (3)	S2—Ni1—P1	97.07 (3)
C15—C16—H16	119.9	N1—Ni1—S1	94.94 (7)
C17—C16—H16	119.9	S2—Ni1—S1	79.06 (3)
C12—C17—C16	120.0 (3)	P1—Ni1—S1	170.83 (3)

N2—C3—C4—C5	−48.3 (4)	C10—C11—N2—C2	125.0 (3)
C3—C4—C5—C10	19.4 (5)	C10—C11—N2—C3	−45.3 (4)
C3—C4—C5—C6	−162.1 (3)	C4—C3—N2—C2	−105.5 (4)
C10—C5—C6—C7	−1.1 (5)	C4—C3—N2—C11	64.7 (4)
C4—C5—C6—C7	−179.7 (4)	C23—C18—P1—C24	26.0 (2)
C5—C6—C7—C8	0.3 (6)	C19—C18—P1—C24	−162.5 (2)
C6—C7—C8—C9	0.9 (6)	C23—C18—P1—C12	134.6 (2)
C7—C8—C9—C10	−1.3 (5)	C19—C18—P1—C12	−53.9 (2)
C6—C5—C10—C9	0.7 (5)	C23—C18—P1—Ni1	−98.25 (19)
C4—C5—C10—C9	179.2 (3)	C19—C18—P1—Ni1	73.2 (2)
C6—C5—C10—C11	178.6 (3)	C25—C24—P1—C18	50.6 (2)
C4—C5—C10—C11	−2.9 (5)	C29—C24—P1—C18	−133.8 (2)
C8—C9—C10—C5	0.5 (5)	C25—C24—P1—C12	−62.8 (2)
C8—C9—C10—C11	−177.4 (3)	C29—C24—P1—C12	112.7 (2)
C5—C10—C11—N2	15.0 (4)	C25—C24—P1—Ni1	167.41 (18)
C9—C10—C11—N2	−167.0 (3)	C29—C24—P1—Ni1	−17.1 (2)
C17—C12—C13—C14	0.1 (4)	C17—C12—P1—C18	−5.7 (3)
P1—C12—C13—C14	177.2 (2)	C13—C12—P1—C18	177.39 (19)
C12—C13—C14—C15	1.0 (4)	C17—C12—P1—C24	106.1 (2)
C13—C14—C15—C16	−0.9 (5)	C13—C12—P1—C24	−70.8 (2)
C14—C15—C16—C17	−0.2 (5)	C17—C12—P1—Ni1	−125.0 (2)
C13—C12—C17—C16	−1.3 (4)	C13—C12—P1—Ni1	58.1 (2)
P1—C12—C17—C16	−178.1 (2)	N2—C2—S1—Ni1	176.0 (3)
C15—C16—C17—C12	1.4 (5)	S2—C2—S1—Ni1	−2.32 (12)
C23—C18—C19—C20	−2.4 (4)	N2—C2—S2—Ni1	−176.0 (2)
P1—C18—C19—C20	−174.1 (2)	S1—C2—S2—Ni1	2.37 (12)
C18—C19—C20—C21	1.4 (4)	C1—N1—Ni1—S2	−139.3 (12)
C19—C20—C21—C22	0.6 (4)	C1—N1—Ni1—P1	30.9 (14)
C20—C21—C22—C23	−1.5 (4)	C1—N1—Ni1—S1	−157.3 (14)
C21—C22—C23—C18	0.4 (4)	C2—S2—Ni1—N1	−20.1 (7)
C19—C18—C23—C22	1.6 (4)	C2—S2—Ni1—P1	169.83 (9)
P1—C18—C23—C22	173.2 (2)	C2—S2—Ni1—S1	−1.76 (9)
C29—C24—C25—C26	1.6 (4)	C18—P1—Ni1—N1	64.00 (11)
P1—C24—C25—C26	177.2 (2)	C24—P1—Ni1—N1	−53.51 (11)
C24—C25—C26—C27	−1.3 (5)	C12—P1—Ni1—N1	−174.89 (12)
C25—C26—C27—C28	0.2 (5)	C18—P1—Ni1—S2	−117.09 (9)
C26—C27—C28—C29	0.6 (5)	C24—P1—Ni1—S2	125.41 (9)
C25—C24—C29—C28	−0.8 (4)	C12—P1—Ni1—S2	4.03 (9)
P1—C24—C29—C28	−176.4 (2)	C18—P1—Ni1—S1	−52.7 (2)
C27—C28—C29—C24	−0.3 (4)	C24—P1—Ni1—S1	−170.20 (18)
S3—C1—N1—Ni1	46 (9)	C12—P1—Ni1—S1	68.4 (2)
S1—C2—N2—C11	−175.1 (2)	C2—S1—Ni1—N1	179.78 (11)
S2—C2—N2—C11	3.0 (4)	C2—S1—Ni1—S2	1.77 (9)
S1—C2—N2—C3	−5.8 (4)	C2—S1—Ni1—P1	−63.9 (2)
S2—C2—N2—C3	172.3 (2)

Experimental details

Crystal data
Chemical formula	[Ni(C₁₀H₁₀NS₂)(NCS)(C₁₈H₁₅P)]
M_r	587.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	292
a, b, c (Å)	13.7981 (4), 13.1429 (4), 14.9447 (4)
β (°)	91.693 (2)
V (Å³)	2708.99 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker KAPPA APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 1999)
T_min, T_max	0.783, 0.861
No. of measured, independent and observed [I > 2σ(I)] reflections	33862, 7287, 5132
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.123, 1.03
No. of reflections	7287
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.30

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)', SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

N1—Ni1	1.867 (2)	S1—Ni1	2.218 (1)
P1—Ni1	2.1874 (6)	S2—Ni1	2.162 (1)

Acknowledgements

ST thanks the SAIF, Indian Institute of Technolgy, Chennai, for the data collection.

References

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