Crystal structure of chlorido­{tris­[2-(iso­propyl­sulfan­yl)phen­yl]phosphane-κ4P,S,S′,S′′}nickel(II) tri­fluoro­methane­sulfonate

Takeda, N.; Oma, R.; Unno, M.

doi:10.1107/S2056989019002068

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ISSN: 2056-9890

Volume 75| Part 3| March 2019| Pages 350-353

https://doi.org/10.1107/S2056989019002068

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Crystal structure of chlorido{tris[2-(isopropylsulfanyl)phenyl]phosphane-κ⁴P,S,S′,S′′}nickel(II) trifluoromethanesulfonate

Nobuhiro Takeda,^a ^* Rin Oma ^a and Masafumi Unno ^a

^aGraduate School of Science and Technology, Gunma University, 1-5-1 Tenjin-cho, Kiryu, Gunma 376-8515, Japan
^*Correspondence e-mail: ntakeda@gunma-u.ac.jp

Edited by H. Ishida, Okayama University, Japan (Received 28 November 2018; accepted 6 February 2019; online 12 February 2019)

The complex cation of the title compound, [NiCl{P(C₆H₄-2-S-i-Pr)₃}](CF₃SO₃), has a slightly distorted trigonal–bipyramidal coordination geometry in which three S atoms are located in the equatorial plane, and one P and one Cl atom in the apical positions. In the cation, there are two intramolecular C—H⋯S hydrogen bonds. In the crystal, there are some intermolecular C—H⋯O and C—H⋯F hydrogen bonds formed between the cation and the anion. The trifluoromethanesulfonate anion and one of the methyl groups are both disordered over two sets of sites with occupancies of 0.629 (17):0.371 (17) and 0.786 (14):0.214 (14), respectively.

Keywords: crystal structure; nickel; five-coordinate; tripodal tetradentate ligand; phosphine; thioether.

CCDC reference: 1895701

1. Chemical context

Unusual five-coordinate nickel(II) complexes have been often obtained by use of polydentate ligands such as tripodal tetradentate ligands (Orioli, 1971 ; Morassi et al., 1973 ; Hierso et al., 2003 ). A variety of tripodal tetradentate ligands having phosphines and/or amines as coordinating sites have been used for the synthesis of five-coordinate nickel(II) complexes. However, for PS₃-type tripodal tetradentate ligands in which three thioether moieties are tethered to a phosphine moiety, only one crystal structure (Haugen & Eisenberg, 1969 ) had been reported before we started our studies. Recently, we have synthesized new PS₃-type tripodal tetradentate ligands, tris(2-isopropylthiophenyl)phosphine, 1a and tris(2-tert-butylthiophenyl)phosphine, 1b (Fig. 1), and reported the syntheses and properties of their group 10 metal complexes (Takeda et al., 2010 , 2016 ). Reaction of 1a with NiCl₂·6H₂O in the presence of NaBF₄ gave the corresponding cationic five-coordinate nickel(II) complex, 2, while the reaction of 1b with NiCl₂·6H₂O resulted in the elimination of t-BuCl to afford a neutral five-coordinate nickel(II) complex, 4 (Fig. 1). In this paper, we describe the structure of the title compound, [NiCl(L)]CF₃SO₃ (L = 1a), 3, which was prepared by reaction of 1a with NiCl₂·6H₂O in the presence of an excess amount of NaCF₃SO₃ (Fig. 1).

Figure 1
Synthesis of nickel(II) complexes bearing the PS₃-type tripodal tetradentate ligand.

2. Structural commentary

The structure of the title compound, 3, is shown in Fig. 2. The triflate anion and one of the methyl groups are each disordered over two sets of sites with occupancies of 0.629 (17):0.371 (17) and 0.786 (14):0.214 (14), respectively. The complex cation of 3 has a five-coordinate slightly distorted trigonal–bipyramidal structure, in which one P atom and one Cl atom coordinate to the nickel center(II) in the apical positions [P1—Ni1—Cl1 177.83 (5)°] and three S atoms are located in the equatorial positions. In addition, there are two weak C—H⋯S intramolecular hydrogen bonds (C26—H26B⋯S1 and C17—H17B⋯S3; Table 1). Table 2 presents selected bond lengths and angles of 3 along with those of the related complexes, complex 2 (Takeda et al., 2010) and the methyl derivative, [NiCl{P(C₆H₄-2-SCH₃)₃}]ClO₄, 5 (Haugen & Eisenberg, 1969). The conformation of the Ni(S-i-Pr)₃ unit of 3 is similar to that of complex 2, but different from that of 5, as shown in Fig. 3. This is probably due to the difference in the bulkiness between the isopropyl and methyl groups. In 3, the Ni1—S3 bond length [2.3072 (13) Å] is slightly longer than the Ni1—S1 and Ni1—S2 bond lengths [2.2574 (12) and 2.2612 (13) Å, respectively], and the S1—Ni1—S2 bond angle [122.83 (5)°] is slightly larger than the S2—Ni1—S3 and S3—Ni1—S1 bond angles [120.87 (5) and 116.04 (5)°, respectively]. This properties suggests that in complex 3 the five-coordinate trigonal–bipyramidal structure slightly approaches a four-coordinate square-planar structure by the elongation of the Ni—S3 bond. This is a similar tendency to the structure of 2, and the deviation from trigonal–bipyramidal structure in 3 is smaller than that in 2. The Ni—S bond lengths of 3 are very close to those of methyl derivative 5, while the S3—Ni—S1 bond angle of 5 [127.1 (3)°] is large as expected from the conformation B (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.95	2.42	3.336 (5)	162
C5—H5⋯O3Bⁱⁱ	0.95	2.55	3.328 (11)	140
C8—H8⋯F2Aⁱⁱⁱ	0.98	2.53	3.318 (14)	138
C8—H8⋯F2Bⁱⁱⁱ	0.98	2.50	3.30 (2)	139
C17—H17B⋯S3	0.98	2.82	3.652 (5)	143
C18—H18B⋯F3B^iv	0.98	2.15	3.099 (12)	162
C20—H20⋯O1ⁱ	0.95	2.58	3.477 (5)	157
C22—H22⋯O2A^v	0.95	2.31	3.127 (12)	144
C26—H26B⋯S1	0.98	2.85	3.762 (6)	156
C27B—H27D⋯O1	0.98	2.46	3.308 (19)	144
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x+1, y, z; (v) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Selected bond distances (Å) and angles (°) in complexes 2, 3 and 5

compounds	3	2^a	5^b
Ni1—P1	2.1124 (11)	2.1108 (7)	2.113 (7)
Ni1—S1	2.2574 (12)	2.2454 (7)	2.242 (8)
Ni1—S2	2.2612 (13)	2.2678 (7)	2.269 (6)
Ni1—S3	2.3072 (13)	2.3510 (7)	2.290 (7)
Ni1—Cl	2.2412 (11)	2.2437 (7)	2.227 (7)

P1—Ni1—Cl1	177.83 (5)	178.60 (3)	178.5 (3)
S2—Ni1—S3	120.87 (5)	109.53 (3)	112.1 (3)
S3—Ni1—S1	116.04 (5)	119.03 (3)	127.1 (3)
S1—Ni1—S2	122.83 (5)	130.74 (3)	120.6 (2)
P1—Ni1—S	88.16 (4)–88.1 (4)	86.9 – 87.5	88.0 – 88.7
Cl1—Ni1—S	89.88 (4)–93.48 (5)	92.0 – 94.5	90.7 – 92.4
Notes: (a) Takeda et al. (2010); (b) Haugen & Eisenberg (1969).

Figure 2
The molecular structure of the title compound, 3. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms and minor disorder components are omitted for clarity.

Figure 3
The conformation diagrams of the Ni(SR)₃ moieties (R = i-Pr or Me) for 3 (A) and 5 (B), viewed along the Ni—Cl bond.

3. Supramolecular features

In the crystal of 3, there are some hydrogen bonds between the cation and the anion (Fig. 4). The cation and the anion are linked into a tape structure along the b-axis direction via C—H⋯O and C—H⋯F hydrogen bonds (C2—H2⋯O1ⁱ, C8—H8⋯F2Aⁱⁱⁱ, C8—H8⋯F2Bⁱⁱⁱ, C20—H20⋯O1ⁱ and C22—H22⋯O2A^v; symmetry codes as in Table 1) . The tapes are further linked by weak C—H⋯O and C—H⋯F hydrogen bonds formed between the cation and the minor component of the disordered anion (C5—H5⋯O3Bⁱⁱ and C18—H18B⋯F3B^iv; Table 1), forming a three-dimensional network (Figs. 5 and 6).

Figure 4
Intramolecular C—H⋯S hydrogen bonds and intermolecular C—H⋯O and C—H⋯F hydrogen bonds (blue dashed lines) in 3. [Symmetry codes: (i) −x + 1, −y + 1, −z + 1; (ii) −x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (iii) x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z + $[{1\over 2}]$ ; (iv) x + 1, y, z; (v) x + $[{1\over 2}]$ , −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ .]

Figure 5
A packing diagram of 3, viewed along the a axis. The C—H⋯O and C—H⋯F hydrogen bonds are shown as dashed lines.

Figure 6
A packing diagram of 3, viewed along the c axis. The C—H⋯O and C—H⋯F hydrogen bonds are shown as dashed lines.

4. Database survey

A search of the Cambridge Structural Database (CSD; Groom et al., 2016 ) using WebCSD found four structures of nickel complexes having three Ni—S, one Ni—P and one Ni—Cl bonds. The structures of the complexes, [NiCl{P(C₆H₄-2-SMe)₃}]ClO₄, 5 (refcode: CMTPPN; Haugen & Eisenberg, 1969) and [NiCl{P(C₆H₄-2-S-i-Pr)₃}]BF₄, 2 (FULMOP; Takeda et al., 2010), are similar to that of the cationic choloridonickel(II) complex 3. The structures of the other two complexes, [Ph₃P=N=PPh₃][NiCl{P(C₆H₃-3-SiMe₃-2-S)₃}] (YETYOM; Lee et al., 2006 ) and [NiCl{P(C₆H₄-2-S)(C₆H₄-2-S-t-Bu)₂}], 4 (EZOQAN; Takeda et al., 2016), are different from that of complex 3. The former is an anionic nickel(III) complex having three thiolato (⁻SR), one chlorido and one phosphine ligands, and the latter, 4, is a neutral nickel(II) complex having two thioether, one thiolato, one chlorido and one phosphine ligands.

5. Synthesis and crystallization

A mixture of tris(2-isopropylthiophenyl)phosphine, 1a (0.141 g, 0.291 mmol), NiCl₂·6H₂O (0.060 g, 0.25 mmol) and NaCF₃SO₃ (0.345 g, 2.01 mmol) in dichloromethane (5 ml) was stirred at room temperature for 4 d. After removal of the solvent under reduced pressure, recrystallization of the residue from a chloroform/hexane solution gave the title compound, 3, as blue crystals (0.168 g, 91%).

M.p. 485 K (decomp.) ¹H NMR (300 MHz, CDCl₃): δ 1.31 (d, ³J_HH = 6.7 Hz, 18H), 3.73 (sepd, ³J_HH = 6.7 Hz, ⁴J_HP = 1.6 Hz, 3H), 7.71 (tdd, ³J_HH = 8.3 Hz, J_HP = 2.2 Hz, ⁴J_HH = 1.0 Hz, 3H), 7.80 (ddd, ³J_HH = 8.3 Hz, ⁴J_HP = 3.3 Hz, ⁴J_HH = 1.0 Hz, 3H), 7.91 (tdd, ³J_HH = 8.3 Hz, J_HP = 2.5 Hz, ⁴J_HH = 1.0 Hz, 3H), 8.68 (dd, ³J_HH = 8.3 Hz, ³J_HP = 8.3 Hz, 3H). ¹³C{¹H} NMR (150 MHz, CDCl₃): δ 22.3 (s, CH₃), 50.7 (s, CH), 132.9 (d, J_CP = 7.2 Hz, CH), 133.4 (d, J_CP = 13.0 Hz, CH), 133.6 (s, CH), 134.8 (s, CH), 135.3 (d, ¹J_CP =63.6 Hz, C), 137.0 (d, ²J_CP = 23.1 Hz, C), the peak of CF₃ could not be detected. ³¹P NMR (162 MHz, CDCl₃): δ 103.3. ¹⁹F NMR (376 MHz, CDCl₃): δ −77.92. IR (KBr): 516.9, 532.3, 551.6, 572.8, 638.4, 673.1, 727.1, 740.6, 779.2, 879.5, 931.6, 1029.9, 1056.9 (S=O), 1116.7, 1157.2 (S=O),1224.7, 1242.1, 1249.8, 1265.2, 1274.9, 1282.6, 1369.4, 1388.7, 1433.0, 1460.0, 1568.0, 1635.5, 2868.0, 2927.7, 2968.2, 3055.0, 3082.0, 3301.9, 3319.3, 3392.6, 3406.1, 3423.4, 3444.6, 3477.4, 3489.0. UV–vis (CHCl₃): λ_max 246 (∊ 35000), 332 (∊ 5700), 474 (∊ 350), 639 nm (∊ 2000). Analysis calculated for C₂₈H₃₃ClF₃NiO₃PS₄: C 46.20, H 4.57%. Found: C 45.38, H 4.55%.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The H atoms were positioned geometrically (C—H = 0.95–1.00 Å) and refined as riding atoms with U_iso(H) =1.5U_eq(C) for methyl or 1.2U_eq(C) for aromatic and methine H atoms. The methyl groups were allowed to rotate freely around the C—C bond. The triflate anion exhibits disorder and was modelled with occupancies of 0.629 (17) and 0.371 (17). The geometric parameters of the minor component were restrained to be similar to those of the major component by using SAME restraint. In addition, one of the methyl groups in the complex cation exhibits disorder and was modelled with occupancies of 0.786 (14) and 0.214 (14). The C25—C27A and C25—C27B bond lengths were restrained to be equal to each other by using SADI restraint.

Table 3
Experimental details

Crystal data
Chemical formula	[NiCl(C₂₇H₃₃PS₃)](CF₃SO₃)
M_r	727.91
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	13.428 (3), 14.008 (3), 17.110 (3)
β (°)	93.164 (4)
V (Å³)	3213.5 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.04
Crystal size (mm)	0.10 × 0.08 × 0.02

Data collection
Diffractometer	Rigaku CrystalClear-SM Expert 2.1 b29
Absorption correction	Numerical (CrystalClear; Rigaku, 2013 )
T_min, T_max	0.924, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	51723, 7359, 5054
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.144, 1.08
No. of reflections	7359
No. of parameters	451
No. of restraints	20
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.35
Computer programs: CrystalClear (Rigaku, 2013), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), Yadokari-XG (Wakita, 2001 ; Kabuto et al., 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1895701

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989019002068/is5507sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019002068/is5507Isup2.hkl

checkCIF report

Computing details top

Data collection: CrystalClear (Rigaku, 2013); cell refinement: CrystalClear (Rigaku, 2013); data reduction: CrystalClear (Rigaku, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: Yadokari-XG (Wakita, 2001; Kabuto et al., 2009); software used to prepare material for publication: Yadokari-XG (Wakita, 2001; Kabuto et al., 2009) and publCIF (Westrip, 2010).

Chlorido{tris[2-(isopropylsulfanyl)phenyl]phosphane-κ⁴P,S,S',S''}nickel(II) trifluoromethanesulfonate top

Crystal data top

[NiCl(C₂₇H₃₃PS₃)](CF₃SO₃)	F(000) = 1504
M_r = 727.91	D_x = 1.505 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
a = 13.428 (3) Å	Cell parameters from 5728 reflections
b = 14.008 (3) Å	θ = 2.8–27.5°
c = 17.110 (3) Å	µ = 1.04 mm⁻¹
β = 93.164 (4)°	T = 120 K
V = 3213.5 (11) Å³	Prism, blue
Z = 4	0.10 × 0.08 × 0.02 mm

Data collection top

Rigaku CrystalClear-SM Expert 2.1 b29 diffractometer	7359 independent reflections
Radiation source: Rotating Anode	5054 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.096
Detector resolution: 5.8140 pixels mm^-1	θ_max = 27.5°, θ_min = 2.8°
profile data from ω–scans	h = −17→17
Absorption correction: numerical (CrystalClear; Rigaku, 2013)	k = −18→18
T_min = 0.924, T_max = 0.971	l = −22→22
51723 measured reflections

Refinement top

Refinement on F²	20 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.0517P)² + 5.7574P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
7359 reflections	Δρ_max = 0.75 e Å⁻³
451 parameters	Δρ_min = −0.35 e Å⁻³

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.75663 (4)	0.31726 (4)	0.35830 (3)	0.02972 (15)
Cl1	0.77545 (8)	0.29069 (9)	0.23080 (6)	0.0409 (3)
P1	0.73682 (7)	0.33699 (7)	0.47886 (5)	0.0246 (2)
C1	0.6229 (3)	0.2789 (3)	0.5066 (2)	0.0262 (8)
C2	0.5845 (3)	0.2845 (3)	0.5811 (2)	0.0321 (9)
H2	0.6179	0.3205	0.6216	0.039*
C3	0.4967 (3)	0.2363 (3)	0.5944 (3)	0.0384 (10)
H3	0.4706	0.2389	0.6448	0.046*
C4	0.4466 (3)	0.1846 (3)	0.5360 (3)	0.0381 (10)
H4	0.3872	0.1516	0.5468	0.046*
C5	0.4822 (3)	0.1805 (3)	0.4619 (3)	0.0358 (10)
H5	0.4465	0.1470	0.4210	0.043*
C6	0.5721 (3)	0.2269 (3)	0.4482 (2)	0.0274 (8)
S1	0.61937 (8)	0.22394 (8)	0.35266 (6)	0.0304 (2)
C7	0.6643 (3)	0.0991 (3)	0.3441 (3)	0.0386 (10)
H7	0.7114	0.0985	0.3008	0.046*
C8	0.7218 (4)	0.0635 (4)	0.4164 (3)	0.0491 (12)
H8	0.6777	0.0613	0.4601	0.074*
H8A	0.7778	0.1066	0.4294	0.074*
H8B	0.7473	−0.0008	0.4067	0.074*
C9	0.5777 (4)	0.0336 (4)	0.3189 (3)	0.0570 (14)
H9	0.6037	−0.0287	0.3038	0.085*
H9A	0.5396	0.0620	0.2743	0.085*
H9B	0.5342	0.0254	0.3625	0.085*
C10	0.8429 (3)	0.2904 (3)	0.5377 (2)	0.0297 (9)
C11	0.8506 (4)	0.2885 (3)	0.6188 (2)	0.0364 (10)
H11	0.7951	0.3060	0.6479	0.044*
C12	0.9387 (4)	0.2611 (4)	0.6570 (3)	0.0460 (12)
H12	0.9448	0.2618	0.7126	0.055*
C13	1.0190 (4)	0.2325 (4)	0.6148 (3)	0.0515 (13)
H13	1.0798	0.2145	0.6418	0.062*
C14	1.0113 (3)	0.2299 (4)	0.5342 (3)	0.0471 (12)
H14	1.0653	0.2075	0.5056	0.057*
C15	0.9229 (3)	0.2607 (3)	0.4950 (3)	0.0364 (10)
S2	0.91100 (8)	0.26050 (9)	0.39095 (6)	0.0383 (3)
C16	1.0134 (4)	0.3448 (4)	0.3714 (3)	0.0515 (13)
H16	1.0729	0.3224	0.4041	0.062*
C17	0.9930 (4)	0.4436 (4)	0.3978 (3)	0.0529 (13)
H17	1.0532	0.4825	0.3946	0.079*
H17A	0.9732	0.4421	0.4521	0.079*
H17B	0.9390	0.4713	0.3643	0.079*
C18	1.0401 (4)	0.3352 (5)	0.2900 (3)	0.0659 (16)
H18	0.9819	0.3502	0.2550	0.099*
H18A	1.0617	0.2696	0.2805	0.099*
H18B	1.0945	0.3794	0.2799	0.099*
C19	0.7307 (3)	0.4636 (3)	0.5007 (2)	0.0270 (8)
C20	0.7291 (3)	0.5015 (3)	0.5767 (2)	0.0297 (9)
H20	0.7287	0.4601	0.6206	0.036*
C21	0.7283 (3)	0.5992 (3)	0.5871 (3)	0.0341 (9)
H21	0.7258	0.6248	0.6383	0.041*
C22	0.7312 (3)	0.6603 (3)	0.5236 (3)	0.0370 (10)
H22	0.7312	0.7274	0.5315	0.044*
C23	0.7340 (3)	0.6238 (3)	0.4487 (3)	0.0372 (10)
H23	0.7375	0.6657	0.4053	0.045*
C24	0.7317 (3)	0.5263 (3)	0.4371 (2)	0.0288 (9)
S3	0.72947 (8)	0.47865 (8)	0.34063 (6)	0.0310 (2)
C25	0.6003 (3)	0.5122 (5)	0.3077 (3)	0.0551 (15)
H25A	0.5974	0.5834	0.3110	0.066*	0.786 (14)
H25B	0.5936	0.4535	0.2745	0.066*	0.214 (14)
C26	0.5214 (3)	0.4751 (4)	0.3611 (3)	0.0459 (12)
H26	0.4550	0.4935	0.3396	0.069*
H26A	0.5329	0.5027	0.4135	0.069*
H26B	0.5257	0.4054	0.3645	0.069*
C27A	0.5825 (5)	0.4890 (6)	0.2262 (3)	0.049 (2)	0.786 (14)
H27A	0.5843	0.4195	0.2195	0.074*	0.786 (14)
H27B	0.6342	0.5184	0.1959	0.074*	0.786 (14)
H27C	0.5170	0.5132	0.2076	0.074*	0.786 (14)
C27B	0.5769 (15)	0.5677 (16)	0.2455 (12)	0.040 (7)	0.214 (14)
H27D	0.5064	0.5589	0.2292	0.059*	0.214 (14)
H27E	0.6184	0.5502	0.2024	0.059*	0.214 (14)
H27F	0.5887	0.6348	0.2596	0.059*	0.214 (14)
S4A	0.2594 (6)	0.5996 (6)	0.1890 (4)	0.0617 (17)	0.629 (17)
O1	0.3353 (3)	0.6108 (2)	0.25204 (19)	0.0508 (9)
O2A	0.2747 (16)	0.6526 (8)	0.1192 (6)	0.119 (6)	0.629 (17)
O3A	0.1589 (6)	0.6058 (12)	0.2106 (7)	0.114 (6)	0.629 (17)
C28A	0.2734 (13)	0.4774 (10)	0.1571 (6)	0.061 (6)	0.629 (17)
F1A	0.3485 (7)	0.4632 (8)	0.1181 (5)	0.070 (2)	0.629 (17)
F2A	0.1947 (10)	0.4527 (12)	0.1075 (7)	0.104 (5)	0.629 (17)
F3A	0.2727 (9)	0.4177 (5)	0.2155 (4)	0.083 (3)	0.629 (17)
S4B	0.2809 (6)	0.6234 (5)	0.1799 (4)	0.0279 (14)	0.371 (17)
O2B	0.3381 (11)	0.6469 (12)	0.1159 (7)	0.056 (4)	0.371 (17)
O3B	0.1917 (9)	0.6754 (11)	0.1844 (6)	0.055 (4)	0.371 (17)
C28B	0.2460 (16)	0.4994 (15)	0.1619 (11)	0.060 (9)	0.371 (17)
F1B	0.320 (2)	0.4458 (15)	0.152 (2)	0.160 (17)	0.371 (17)
F2B	0.1807 (14)	0.4953 (11)	0.0986 (11)	0.061 (4)	0.371 (17)
F3B	0.1961 (17)	0.4693 (15)	0.2206 (8)	0.116 (10)	0.371 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0264 (3)	0.0409 (3)	0.0222 (3)	−0.0057 (2)	0.0052 (2)	−0.0053 (2)
Cl1	0.0365 (6)	0.0615 (8)	0.0254 (5)	−0.0050 (5)	0.0077 (4)	−0.0094 (5)
P1	0.0243 (5)	0.0283 (5)	0.0214 (5)	−0.0028 (4)	0.0023 (4)	−0.0017 (4)
C1	0.024 (2)	0.027 (2)	0.028 (2)	0.0007 (16)	0.0046 (15)	0.0029 (16)
C2	0.035 (2)	0.033 (2)	0.029 (2)	−0.0028 (19)	0.0064 (17)	−0.0028 (17)
C3	0.044 (3)	0.035 (2)	0.038 (2)	0.001 (2)	0.019 (2)	0.0055 (19)
C4	0.030 (2)	0.034 (2)	0.051 (3)	−0.0036 (19)	0.014 (2)	0.006 (2)
C5	0.031 (2)	0.034 (2)	0.042 (2)	−0.0056 (19)	0.0038 (18)	−0.0005 (19)
C6	0.022 (2)	0.029 (2)	0.032 (2)	−0.0018 (17)	0.0046 (16)	0.0003 (16)
S1	0.0306 (5)	0.0352 (6)	0.0255 (5)	−0.0062 (4)	0.0021 (4)	−0.0049 (4)
C7	0.045 (3)	0.035 (2)	0.038 (2)	−0.005 (2)	0.014 (2)	−0.0136 (19)
C8	0.056 (3)	0.042 (3)	0.051 (3)	0.008 (2)	0.014 (2)	0.002 (2)
C9	0.065 (4)	0.038 (3)	0.068 (4)	−0.014 (3)	0.009 (3)	−0.020 (3)
C10	0.028 (2)	0.027 (2)	0.034 (2)	−0.0057 (17)	−0.0026 (17)	−0.0012 (16)
C11	0.047 (3)	0.032 (2)	0.030 (2)	0.001 (2)	−0.0038 (19)	0.0004 (17)
C12	0.052 (3)	0.046 (3)	0.039 (3)	0.001 (2)	−0.010 (2)	0.005 (2)
C13	0.039 (3)	0.059 (3)	0.054 (3)	−0.002 (3)	−0.015 (2)	0.009 (3)
C14	0.027 (2)	0.063 (3)	0.052 (3)	0.005 (2)	0.001 (2)	0.008 (2)
C15	0.027 (2)	0.041 (3)	0.041 (2)	−0.0025 (19)	−0.0005 (18)	0.0003 (19)
S2	0.0317 (6)	0.0464 (7)	0.0379 (6)	0.0025 (5)	0.0105 (4)	−0.0053 (5)
C16	0.028 (2)	0.068 (4)	0.061 (3)	−0.005 (2)	0.018 (2)	0.002 (3)
C17	0.040 (3)	0.064 (4)	0.055 (3)	−0.022 (3)	0.007 (2)	−0.005 (3)
C18	0.057 (4)	0.091 (5)	0.052 (3)	−0.002 (3)	0.020 (3)	−0.004 (3)
C19	0.0209 (19)	0.030 (2)	0.031 (2)	−0.0013 (16)	0.0051 (15)	−0.0012 (16)
C20	0.025 (2)	0.035 (2)	0.029 (2)	−0.0009 (17)	0.0050 (16)	0.0011 (16)
C21	0.032 (2)	0.033 (2)	0.038 (2)	−0.0042 (19)	0.0028 (18)	−0.0078 (18)
C22	0.031 (2)	0.029 (2)	0.051 (3)	0.0009 (18)	0.0029 (19)	−0.0011 (19)
C23	0.036 (2)	0.031 (2)	0.044 (3)	0.0018 (19)	0.0061 (19)	0.0096 (19)
C24	0.025 (2)	0.035 (2)	0.027 (2)	−0.0007 (17)	0.0060 (16)	0.0035 (16)
S3	0.0256 (5)	0.0430 (6)	0.0247 (5)	−0.0003 (4)	0.0048 (4)	0.0063 (4)
C25	0.029 (3)	0.096 (4)	0.040 (3)	0.009 (3)	0.002 (2)	0.022 (3)
C26	0.024 (2)	0.067 (3)	0.046 (3)	0.005 (2)	0.0067 (19)	0.014 (2)
C27A	0.034 (3)	0.079 (6)	0.035 (3)	−0.003 (3)	0.000 (3)	−0.005 (3)
C27B	0.022 (11)	0.032 (14)	0.065 (16)	0.010 (9)	0.010 (10)	0.005 (11)
S4A	0.082 (4)	0.063 (3)	0.0385 (19)	0.032 (3)	−0.009 (2)	−0.001 (2)
O1	0.059 (2)	0.054 (2)	0.0383 (18)	−0.0034 (18)	−0.0051 (16)	0.0042 (15)
O2A	0.229 (17)	0.066 (6)	0.057 (6)	0.046 (10)	−0.024 (8)	0.009 (4)
O3A	0.059 (5)	0.171 (15)	0.111 (8)	0.051 (7)	−0.012 (5)	−0.075 (9)
C28A	0.078 (12)	0.074 (12)	0.033 (7)	−0.028 (10)	0.015 (7)	−0.016 (8)
F1A	0.079 (5)	0.070 (5)	0.065 (4)	0.014 (3)	0.029 (4)	−0.008 (3)
F2A	0.093 (7)	0.151 (12)	0.066 (6)	−0.020 (8)	−0.005 (5)	−0.050 (8)
F3A	0.135 (8)	0.055 (4)	0.061 (4)	−0.023 (5)	0.026 (4)	0.002 (3)
S4B	0.036 (2)	0.032 (3)	0.015 (2)	−0.0002 (19)	0.0013 (14)	0.0037 (16)
O2B	0.069 (9)	0.068 (9)	0.031 (6)	−0.027 (8)	0.007 (6)	0.018 (5)
O3B	0.051 (7)	0.065 (9)	0.046 (6)	0.024 (6)	−0.013 (5)	−0.013 (6)
C28B	0.048 (12)	0.060 (13)	0.070 (19)	0.008 (10)	−0.023 (11)	0.021 (11)
F1B	0.25 (4)	0.056 (12)	0.17 (3)	0.068 (17)	−0.03 (2)	−0.033 (16)
F2B	0.054 (7)	0.066 (9)	0.061 (7)	−0.004 (6)	−0.017 (5)	−0.025 (6)
F3B	0.153 (18)	0.106 (15)	0.086 (9)	−0.096 (15)	−0.020 (9)	0.047 (8)

Geometric parameters (Å, º) top

Ni1—P1	2.1124 (11)	C17—H17A	0.9800
Ni1—Cl1	2.2412 (11)	C17—H17B	0.9800
Ni1—S1	2.2574 (12)	C18—H18	0.9800
Ni1—S2	2.2612 (13)	C18—H18A	0.9800
Ni1—S3	2.3072 (13)	C18—H18B	0.9800
P1—C19	1.815 (4)	C19—C24	1.398 (5)
P1—C1	1.819 (4)	C19—C20	1.406 (5)
P1—C10	1.820 (4)	C20—C21	1.380 (6)
C1—C6	1.385 (5)	C20—H20	0.9500
C1—C2	1.403 (5)	C21—C22	1.385 (6)
C2—C3	1.388 (6)	C21—H21	0.9500
C2—H2	0.9500	C22—C23	1.382 (6)
C3—C4	1.379 (6)	C22—H22	0.9500
C3—H3	0.9500	C23—C24	1.380 (6)
C4—C5	1.381 (6)	C23—H23	0.9500
C4—H4	0.9500	C24—S3	1.779 (4)
C5—C6	1.401 (6)	S3—C25	1.854 (5)
C5—H5	0.9500	C25—C27B	1.341 (15)
C6—S1	1.787 (4)	C25—C27A	1.440 (7)
S1—C7	1.858 (5)	C25—C26	1.528 (6)
C7—C8	1.507 (7)	C25—H25A	1.0000
C7—C9	1.524 (7)	C25—H25B	1.0000
C7—H7	1.0000	C26—H26	0.9800
C8—H8	0.9800	C26—H26A	0.9800
C8—H8A	0.9800	C26—H26B	0.9800
C8—H8B	0.9800	C27A—H27A	0.9800
C9—H9	0.9800	C27A—H27B	0.9800
C9—H9A	0.9800	C27A—H27C	0.9800
C9—H9B	0.9800	C27B—H27D	0.9800
C10—C11	1.386 (6)	C27B—H27E	0.9800
C10—C15	1.396 (6)	C27B—H27F	0.9800
C11—C12	1.375 (6)	S4A—O3A	1.421 (8)
C11—H11	0.9500	S4A—O2A	1.432 (9)
C12—C13	1.390 (7)	S4A—O1	1.450 (7)
C12—H12	0.9500	S4A—C28A	1.809 (14)
C13—C14	1.378 (7)	O1—S4B	1.410 (8)
C13—H13	0.9500	C28A—F1A	1.255 (19)
C14—C15	1.398 (6)	C28A—F3A	1.302 (13)
C14—H14	0.9500	C28A—F2A	1.364 (14)
C15—S2	1.779 (4)	S4B—O3B	1.408 (11)
S2—C16	1.857 (5)	S4B—O2B	1.410 (10)
C16—C18	1.462 (7)	S4B—C28B	1.822 (17)
C16—C17	1.487 (8)	C28B—F1B	1.26 (2)
C16—H16	1.0000	C28B—F3B	1.307 (17)
C17—H17	0.9800	C28B—F2B	1.357 (17)

P1—Ni1—Cl1	177.83 (5)	H17—C17—H17A	109.5
P1—Ni1—S1	88.34 (4)	C16—C17—H17B	109.5
Cl1—Ni1—S1	89.88 (4)	H17—C17—H17B	109.5
P1—Ni1—S2	88.16 (4)	H17A—C17—H17B	109.5
Cl1—Ni1—S2	91.78 (4)	C16—C18—H18	109.5
S1—Ni1—S2	122.83 (5)	C16—C18—H18A	109.5
P1—Ni1—S3	88.41 (4)	H18—C18—H18A	109.5
Cl1—Ni1—S3	93.48 (5)	C16—C18—H18B	109.5
S1—Ni1—S3	116.04 (5)	H18—C18—H18B	109.5
S2—Ni1—S3	120.87 (5)	H18A—C18—H18B	109.5
C19—P1—C1	109.59 (18)	C24—C19—C20	119.0 (4)
C19—P1—C10	106.25 (18)	C24—C19—P1	116.8 (3)
C1—P1—C10	109.81 (18)	C20—C19—P1	124.2 (3)
C19—P1—Ni1	109.76 (13)	C21—C20—C19	119.6 (4)
C1—P1—Ni1	110.45 (13)	C21—C20—H20	120.2
C10—P1—Ni1	110.90 (14)	C19—C20—H20	120.2
C6—C1—C2	119.5 (4)	C20—C21—C22	120.8 (4)
C6—C1—P1	115.8 (3)	C20—C21—H21	119.6
C2—C1—P1	124.7 (3)	C22—C21—H21	119.6
C3—C2—C1	118.7 (4)	C23—C22—C21	120.1 (4)
C3—C2—H2	120.7	C23—C22—H22	120.0
C1—C2—H2	120.7	C21—C22—H22	120.0
C4—C3—C2	121.4 (4)	C24—C23—C22	119.9 (4)
C4—C3—H3	119.3	C24—C23—H23	120.1
C2—C3—H3	119.3	C22—C23—H23	120.1
C3—C4—C5	120.5 (4)	C23—C24—C19	120.7 (4)
C3—C4—H4	119.7	C23—C24—S3	120.2 (3)
C5—C4—H4	119.7	C19—C24—S3	119.1 (3)
C4—C5—C6	118.6 (4)	C24—S3—C25	98.9 (2)
C4—C5—H5	120.7	C24—S3—Ni1	104.55 (14)
C6—C5—H5	120.7	C25—S3—Ni1	115.2 (2)
C1—C6—C5	121.2 (4)	C27B—C25—C26	122.1 (9)
C1—C6—S1	119.1 (3)	C27A—C25—C26	114.8 (5)
C5—C6—S1	119.7 (3)	C27B—C25—S3	124.2 (9)
C6—S1—C7	103.16 (19)	C27A—C25—S3	109.8 (4)
C6—S1—Ni1	106.14 (13)	C26—C25—S3	113.6 (3)
C7—S1—Ni1	106.29 (15)	C27A—C25—H25A	105.9
C8—C7—C9	112.4 (4)	C26—C25—H25A	105.9
C8—C7—S1	113.6 (3)	S3—C25—H25A	105.9
C9—C7—S1	110.1 (3)	C27B—C25—H25B	91.0
C8—C7—H7	106.8	C26—C25—H25B	91.0
C9—C7—H7	106.8	S3—C25—H25B	91.0
S1—C7—H7	106.8	C25—C26—H26	109.5
C7—C8—H8	109.5	C25—C26—H26A	109.5
C7—C8—H8A	109.5	H26—C26—H26A	109.5
H8—C8—H8A	109.5	C25—C26—H26B	109.5
C7—C8—H8B	109.5	H26—C26—H26B	109.5
H8—C8—H8B	109.5	H26A—C26—H26B	109.5
H8A—C8—H8B	109.5	C25—C27A—H27A	109.5
C7—C9—H9	109.5	C25—C27A—H27B	109.5
C7—C9—H9A	109.5	H27A—C27A—H27B	109.5
H9—C9—H9A	109.5	C25—C27A—H27C	109.5
C7—C9—H9B	109.5	H27A—C27A—H27C	109.5
H9—C9—H9B	109.5	H27B—C27A—H27C	109.5
H9A—C9—H9B	109.5	C25—C27B—H27D	109.5
C11—C10—C15	120.1 (4)	C25—C27B—H27E	109.5
C11—C10—P1	125.0 (3)	H27D—C27B—H27E	109.5
C15—C10—P1	114.7 (3)	C25—C27B—H27F	109.5
C12—C11—C10	119.7 (4)	H27D—C27B—H27F	109.5
C12—C11—H11	120.1	H27E—C27B—H27F	109.5
C10—C11—H11	120.1	O3A—S4A—O2A	111.6 (8)
C11—C12—C13	120.4 (4)	O3A—S4A—O1	116.0 (5)
C11—C12—H12	119.8	O2A—S4A—O1	115.9 (7)
C13—C12—H12	119.8	O3A—S4A—C28A	104.6 (8)
C14—C13—C12	120.7 (4)	O2A—S4A—C28A	102.6 (6)
C14—C13—H13	119.6	O1—S4A—C28A	104.2 (6)
C12—C13—H13	119.6	F1A—C28A—F3A	110.3 (14)
C13—C14—C15	119.1 (5)	F1A—C28A—F2A	104.3 (11)
C13—C14—H14	120.4	F3A—C28A—F2A	106.0 (10)
C15—C14—H14	120.4	F1A—C28A—S4A	114.2 (9)
C10—C15—C14	119.9 (4)	F3A—C28A—S4A	111.8 (9)
C10—C15—S2	119.7 (3)	F2A—C28A—S4A	109.7 (12)
C14—C15—S2	120.4 (3)	O3B—S4B—O1	114.7 (7)
C15—S2—C16	98.8 (2)	O3B—S4B—O2B	115.0 (9)
C15—S2—Ni1	106.11 (14)	O1—S4B—O2B	115.6 (7)
C16—S2—Ni1	114.20 (18)	O3B—S4B—C28B	106.9 (9)
C18—C16—C17	115.8 (5)	O1—S4B—C28B	98.3 (7)
C18—C16—S2	109.6 (4)	O2B—S4B—C28B	103.7 (9)
C17—C16—S2	112.7 (3)	F1B—C28B—F3B	111 (2)
C18—C16—H16	106.0	F1B—C28B—F2B	110.3 (19)
C17—C16—H16	106.0	F3B—C28B—F2B	105.3 (16)
S2—C16—H16	106.0	F1B—C28B—S4B	113.1 (17)
C16—C17—H17	109.5	F3B—C28B—S4B	108.4 (13)
C16—C17—H17A	109.5	F2B—C28B—S4B	109.0 (14)

C19—P1—C1—C6	125.3 (3)	C15—S2—C16—C17	−66.9 (4)
C10—P1—C1—C6	−118.4 (3)	Ni1—S2—C16—C17	45.3 (4)
Ni1—P1—C1—C6	4.2 (3)	C1—P1—C19—C24	−116.7 (3)
C19—P1—C1—C2	−54.1 (4)	C10—P1—C19—C24	124.7 (3)
C10—P1—C1—C2	62.3 (4)	Ni1—P1—C19—C24	4.8 (3)
Ni1—P1—C1—C2	−175.1 (3)	C1—P1—C19—C20	66.1 (4)
C6—C1—C2—C3	0.9 (6)	C10—P1—C19—C20	−52.5 (4)
P1—C1—C2—C3	−179.8 (3)	Ni1—P1—C19—C20	−172.5 (3)
C1—C2—C3—C4	−0.8 (7)	C24—C19—C20—C21	0.2 (6)
C2—C3—C4—C5	−0.8 (7)	P1—C19—C20—C21	177.5 (3)
C3—C4—C5—C6	2.4 (7)	C19—C20—C21—C22	−1.4 (6)
C2—C1—C6—C5	0.7 (6)	C20—C21—C22—C23	0.5 (7)
P1—C1—C6—C5	−178.6 (3)	C21—C22—C23—C24	1.4 (7)
C2—C1—C6—S1	177.8 (3)	C22—C23—C24—C19	−2.6 (6)
P1—C1—C6—S1	−1.6 (4)	C22—C23—C24—S3	177.1 (3)
C4—C5—C6—C1	−2.3 (6)	C20—C19—C24—C23	1.7 (6)
C4—C5—C6—S1	−179.4 (3)	P1—C19—C24—C23	−175.7 (3)
C1—C6—S1—C7	110.1 (3)	C20—C19—C24—S3	−177.9 (3)
C5—C6—S1—C7	−72.9 (4)	P1—C19—C24—S3	4.7 (4)
C1—C6—S1—Ni1	−1.5 (4)	C23—C24—S3—C25	−71.4 (4)
C5—C6—S1—Ni1	175.6 (3)	C19—C24—S3—C25	108.3 (4)
C6—S1—C7—C8	−43.9 (4)	C23—C24—S3—Ni1	169.5 (3)
Ni1—S1—C7—C8	67.5 (3)	C19—C24—S3—Ni1	−10.9 (3)
C6—S1—C7—C9	83.1 (4)	C24—S3—C25—C27B	121.1 (14)
Ni1—S1—C7—C9	−165.4 (3)	Ni1—S3—C25—C27B	−128.1 (14)
C19—P1—C10—C11	63.9 (4)	C24—S3—C25—C27A	174.4 (5)
C1—P1—C10—C11	−54.5 (4)	Ni1—S3—C25—C27A	−74.8 (5)
Ni1—P1—C10—C11	−176.9 (3)	C24—S3—C25—C26	−55.5 (5)
C19—P1—C10—C15	−112.0 (3)	Ni1—S3—C25—C26	55.3 (5)
C1—P1—C10—C15	129.6 (3)	O3A—S4A—C28A—F1A	163.6 (10)
Ni1—P1—C10—C15	7.2 (4)	O2A—S4A—C28A—F1A	47.0 (12)
C15—C10—C11—C12	2.7 (6)	O1—S4A—C28A—F1A	−74.3 (10)
P1—C10—C11—C12	−172.9 (3)	O3A—S4A—C28A—F3A	−70.4 (13)
C10—C11—C12—C13	−2.0 (7)	O2A—S4A—C28A—F3A	173.0 (12)
C11—C12—C13—C14	−0.8 (8)	O1—S4A—C28A—F3A	51.8 (13)
C12—C13—C14—C15	2.9 (8)	O3A—S4A—C28A—F2A	46.9 (11)
C11—C10—C15—C14	−0.6 (7)	O2A—S4A—C28A—F2A	−69.7 (12)
P1—C10—C15—C14	175.5 (4)	O1—S4A—C28A—F2A	169.1 (9)
C11—C10—C15—S2	178.4 (3)	O3B—S4B—C28B—F1B	176 (2)
P1—C10—C15—S2	−5.5 (5)	O1—S4B—C28B—F1B	−65 (2)
C13—C14—C15—C10	−2.2 (7)	O2B—S4B—C28B—F1B	54 (2)
C13—C14—C15—S2	178.8 (4)	O3B—S4B—C28B—F3B	−61.0 (16)
C10—C15—S2—C16	119.9 (4)	O1—S4B—C28B—F3B	58.1 (15)
C14—C15—S2—C16	−61.1 (4)	O2B—S4B—C28B—F3B	177.1 (14)
C10—C15—S2—Ni1	1.5 (4)	O3B—S4B—C28B—F2B	53.1 (16)
C14—C15—S2—Ni1	−179.5 (4)	O1—S4B—C28B—F2B	172.2 (14)
C15—S2—C16—C18	162.6 (4)	O2B—S4B—C28B—F2B	−68.9 (16)
Ni1—S2—C16—C18	−85.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.95	2.42	3.336 (5)	162
C5—H5···O3Bⁱⁱ	0.95	2.55	3.328 (11)	140
C8—H8···F2Aⁱⁱⁱ	0.98	2.53	3.318 (14)	138
C8—H8···F2Bⁱⁱⁱ	0.98	2.50	3.30 (2)	139
C17—H17B···S3	0.98	2.82	3.652 (5)	143
C18—H18B···F3B^iv	0.98	2.15	3.099 (12)	162
C20—H20···O1ⁱ	0.95	2.58	3.477 (5)	157
C22—H22···O2A^v	0.95	2.31	3.127 (12)	144
C26—H26B···S1	0.98	2.85	3.762 (6)	156
C27B—H27D···O1	0.98	2.46	3.308 (19)	144

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x+1, y, z; (v) x+1/2, −y+3/2, z+1/2.

Selected bond distances (Å) and angles (°) in complexes 2, 3 and 5 top

compounds	3	2^a	5^b
Ni1—P1	2.1124 (11)	2.1108 (7)	2.113 (7)
Ni1—S1	2.2574 (12)	2.2454 (7)	2.242 (8)
Ni1—S2	2.2612 (13)	2.2678 (7)	2.269 (6)
Ni1—S3	2.3072 (13)	2.3510 (7)	2.290 (7)
Ni1—Cl	2.2412 (11)	2.2437 (7)	2.227 (7)

P1—Ni1—Cl	177.83 (5)	178.60 (3)	178.5 (3)
S2—Ni1—S3	120.87 (5)	109.53 (3)	112.1 (3)
S3—Ni1—S1	116.04 (5)	119.03 (3)	127.1 (3)
S1—Ni1—S2	122.83 (5)	130.74 (3)	120.6 (2)
P1—Ni1—S	88.16 (4)–88.1 (4)	86.9 – 87.5	88.0 – 88.7
Cl—Ni1—S	89.88 (4)–93.48 (5)	92.0 – 94.5	90.7 – 92.4

Notes: (a) Takeda et al. (2010); (b) Haugen & Eisenberg (1969).

Funding information

Funding for this research was provided by: Grant-in-Aid for Scientific Research (C) from Japan Society for the Promotion of Science (JSPS), `Development of Innovative Catalytic Processes for Organosilicon Functional Materials' project (PL: K. Sato) from the New Energy and Industrial Technology Development Organization (NEDO).

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