The complex cation of the title compound has a five-coordinate slightly distorted trigonal–bipyramidal structure in which three S atoms are located in the equatorial positions, and one P and one Cl atom in the apical positions.
Keywords: crystal structure, nickel, five-coordinate, tripodal tetradentate ligand, phosphine, thioether
Abstract
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.
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.
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 ▸).
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.
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⋯O3B ii | 0.95 | 2.55 | 3.328 (11) | 140 |
| C8—H8⋯F2A iii | 0.98 | 2.53 | 3.318 (14) | 138 |
| C8—H8⋯F2B iii | 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) 
; (ii) 
; (iii) 
; (iv) 
; (v) 
.
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 |
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.
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⋯F2A iii, C8—H8⋯F2B iii, 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⋯O3B ii 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 + 
, y − , −z + ; (iii) x + , −y + , z + ; (iv) x + 1, y, z; (v) x + , −y + 
, z + .]
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.
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.
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, 3 J HH = 6.7 Hz, 18H), 3.73 (sepd, 3 J HH = 6.7 Hz, 4 J HP = 1.6 Hz, 3H), 7.71 (tdd, 3 J HH = 8.3 Hz, J HP = 2.2 Hz, 4 J HH = 1.0 Hz, 3H), 7.80 (ddd, 3 J HH = 8.3 Hz, 4 J HP = 3.3 Hz, 4 J HH = 1.0 Hz, 3H), 7.91 (tdd, 3 J HH = 8.3 Hz, J HP = 2.5 Hz, 4 J HH = 1.0 Hz, 3H), 8.68 (dd, 3 J HH = 8.3 Hz, 3 J 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, 1 J CP =63.6 Hz, C), 137.0 (d, 2 J 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%.
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[F 2 > 2σ(F 2)], wR(F 2), 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 |
| Δρmax, Δρmin (e Å−3) | 0.75, −0.35 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989019002068/is5507sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019002068/is5507Isup2.hkl
CCDC reference: 1895701
Additional supporting information: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
Crystal data
| [NiCl(C27H33PS3)](CF3SO3) | F(000) = 1504 |
| Mr = 727.91 | Dx = 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
| Rigaku CrystalClear-SM Expert 2.1 b29 diffractometer | 7359 independent reflections |
| Radiation source: Rotating Anode | 5054 reflections with I > 2σ(I) |
| Confocal monochromator | Rint = 0.096 |
| Detector resolution: 5.8140 pixels mm-1 | θmax = 27.5°, θmin = 2.8° |
| profile data from ω–scans | h = −17→17 |
| Absorption correction: numerical (CrystalClear; Rigaku, 2013) | k = −18→18 |
| Tmin = 0.924, Tmax = 0.971 | l = −22→22 |
| 51723 measured reflections |
Refinement
| 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(Fo2) + (0.0517P)2 + 5.7574P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max < 0.001 |
| 7359 reflections | Δρmax = 0.75 e Å−3 |
| 451 parameters | Δρmin = −0.35 e Å−3 |
Special details
| 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)
| x | y | z | Uiso*/Ueq | 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)
| 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)
| 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)
| 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···F3Biv | 0.98 | 2.15 | 3.099 (12) | 162 |
| C20—H20···O1i | 0.95 | 2.58 | 3.477 (5) | 157 |
| C22—H22···O2Av | 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.
Funding Statement
This work was funded by Japan Society for the Promotion of Science grant . New Energy and Industrial Technology Development Organization grant .
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989019002068/is5507sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019002068/is5507Isup2.hkl
CCDC reference: 1895701
Additional supporting information: crystallographic information; 3D view; checkCIF report