Bis(O,O′-diisopropyl dithio­phosphato-κ²S,S′)(1,10-phenanthroline)nickel(II)

The Ni atom in the monomeric title compound, [Ni(C₆H₁₄O₂PS₂)₂(C₁₂H₈N₂)], is within a distorted octa­hedral N₂S₄ geometry, defined by two chelating dithio­phosphate ligands and a chelating 1,10-phenanthroline ligand.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.057
• wR factor = 0.118
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.787     1.000
            Tmin(prime) and Tmax expected:      0.878     0.909
            RR(prime) =      0.815
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.81
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.91
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.909
            Tmax scaled      0.909 Tmin scaled      0.716
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni          (2)       1.68

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

Nickel(II) dithiophosphates, Ni(S₂P(OR)₂)₂, are well known to form stable adducts with pyridine-type ligands (Berdugo & Tiekink, 2006; Berdugo et al., 2006, 2007). In {Ni[S₂P(OⁱPr)₂]₂(1,10-phenanthroline)} (I), Fig. 1, the Ni atom exists within a N₂S₄ donor set defined by a two chelating dithiophosphate ligands and a chelating 1,10-phenanthroline ligand. The dithiophosphate ligands chelate in the symmetric mode with the Ni—S distances lying in the relatively narrow range of 2.4674 (11) to 2.5075 (11) Å. The Ni—N distances are equal within experimental error, i.e. 2.098 (3) and 2.100 (3) Å. The major distortions from the ideal octahedral geometry are related to the acute chelate angles that range from 79.75 (12)° for N1—Ni—N2 to 81.80 (4)° for S1—Ni—S2. The structure conforms closely to other structures of the general formula [Ni(S₂P(OR)₂)₂(1,10-phenanthroline)], R = Me (Shetty & Fernando, 1970), R = Et (Craig et al., 1971) and R = p-tol (Hao et al., 2001).

Related literature

For related literature, see Berdugo & Tiekink (2006); Berdugo et al. (2006, 2007). For related structures, see Shetty & Fernando (1970); Craig et al. (1971); Hao et al. (2001).

For related literature, see: Hoskins & Tiekink (1985); Lai et al. (2004).

S2. Experimental

The title compound was prepared by warming (338 K) the parent nickel dithiophosphate (Hoskins & Tiekink, 1985) with 1,10-phenanthroline (Acros Organics) following a literature procedure in CHCl₃ (40 ml) (Lai et al., 2004). Green crystals were isolated by the slow evaporation (4 days) of a 1:7:2 methanol/ethanol/CHCl₃ solution of the compound; m.p. 569 K. IR (KBr disk): ν(C—O) 1174, ν(P—O) 956, ν(P—S)_asymm 660, ν(P—S)_sym 554 cm^-1.

S3. Refinement

The C-bound H atoms were included in the riding-model approximation with C—H distances = 0.95 to 0.98 Å, and with U_iso(methyl-H) = 1.5U_eq(methyl-C) and U_iso(H) = 1.2U_eq(remaining-C).

Computing details

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: PATTY in DIRDIF (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. Molecular structure and crystallographic numbering scheme for (I). Displacement ellipsoids are shown at the 50% probability level.

Bis(O,O'-diisopropyl dithiophosphato-κ²S,S')(1,10-phenanthroline)nickel(II)

Crystal data

[Ni(C6H14O2PS2)2(C12H8N2)]	F(000) = 1392
Mr = 665.44	Dx = 1.463 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 11263 reflections
a = 14.4115 (17) Å	θ = 2.3–30.4°
b = 11.3618 (11) Å	µ = 1.06 mm^−1
c = 18.582 (2) Å	T = 173 K
β = 96.829 (3)°	Block, green
V = 3021.0 (6) Å^3	0.12 × 0.10 × 0.09 mm
Z = 4

Data collection

Rigaku AFC12κ/SATURN724 diffractometer	6248 independent reflections
Radiation source: fine-focus sealed tube	5770 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω scans	θmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→18
Tmin = 0.787, Tmax = 1	k = −14→14
30553 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + (0.0251P)^2 + 8.8715P] where P = (Fo^2 + 2Fc^2)/3
6248 reflections	(Δ/σ)max = 0.001
334 parameters	Δρmax = 0.67 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni	0.23701 (3)	0.47852 (4)	0.80759 (3)	0.02291 (13)
S1	0.07915 (7)	0.39132 (9)	0.79641 (6)	0.0325 (2)
S2	0.26773 (7)	0.32161 (9)	0.90167 (5)	0.0279 (2)
S3	0.19746 (7)	0.63322 (8)	0.89438 (5)	0.0285 (2)
S4	0.39635 (7)	0.56769 (8)	0.83575 (5)	0.0277 (2)
P1	0.12922 (7)	0.30853 (9)	0.88634 (5)	0.0258 (2)
P2	0.32526 (7)	0.68842 (8)	0.88466 (5)	0.0255 (2)
O1	0.0927 (2)	0.1774 (2)	0.88923 (16)	0.0350 (7)
O2	0.08171 (18)	0.3637 (2)	0.95129 (14)	0.0308 (6)
O3	0.31619 (19)	0.8101 (2)	0.84164 (15)	0.0295 (6)
O4	0.38178 (19)	0.7324 (2)	0.95864 (15)	0.0307 (6)
N1	0.2881 (2)	0.3751 (3)	0.72725 (16)	0.0239 (6)
N2	0.2021 (2)	0.5858 (3)	0.71649 (16)	0.0241 (6)
C1	0.1298 (4)	0.0758 (4)	0.8559 (3)	0.0469 (12)
H1	0.1964	0.0654	0.8772	0.056*
C2	0.1269 (4)	0.0811 (5)	0.7766 (3)	0.0593 (15)
H2A	0.1649	0.1474	0.7634	0.089*
H2B	0.0621	0.0919	0.7548	0.089*
H2C	0.1516	0.0077	0.7589	0.089*
C3	0.0733 (4)	−0.0264 (4)	0.8809 (3)	0.0594 (15)
H3A	0.0766	−0.0254	0.9338	0.089*
H3B	0.0989	−0.1008	0.8652	0.089*
H3C	0.0080	−0.0189	0.8596	0.089*
C4	0.1173 (3)	0.3375 (4)	1.0269 (2)	0.0327 (9)
H4	0.1819	0.3048	1.0284	0.039*
C5	0.1224 (4)	0.4531 (4)	1.0668 (3)	0.0509 (12)
H5A	0.1632	0.5073	1.0442	0.076*
H5B	0.1477	0.4402	1.1175	0.076*
H5C	0.0596	0.4872	1.0647	0.076*
C6	0.0566 (4)	0.2475 (5)	1.0577 (3)	0.0633 (16)
H6A	0.0568	0.1746	1.0295	0.095*
H6B	−0.0074	0.2776	1.0554	0.095*
H6C	0.0809	0.2316	1.1083	0.095*
C7	0.4010 (3)	0.8641 (4)	0.8187 (2)	0.0336 (9)
H7	0.4556	0.8107	0.8317	0.040*
C8	0.3835 (4)	0.8768 (5)	0.7377 (3)	0.0561 (14)
H8A	0.3746	0.7988	0.7154	0.084*
H8B	0.4373	0.9155	0.7200	0.084*
H8C	0.3273	0.9245	0.7247	0.084*
C9	0.4175 (4)	0.9787 (4)	0.8586 (3)	0.0528 (13)
H9A	0.4308	0.9633	0.9107	0.079*
H9B	0.3616	1.0281	0.8495	0.079*
H9C	0.4707	1.0194	0.8416	0.079*
C10	0.4348 (3)	0.6570 (4)	1.0117 (2)	0.0333 (9)
H10	0.4832	0.6141	0.9876	0.040*
C11	0.3739 (3)	0.5684 (4)	1.0438 (2)	0.0370 (10)
H11A	0.3453	0.5159	1.0056	0.056*
H11B	0.3248	0.6095	1.0661	0.056*
H11C	0.4120	0.5220	1.0808	0.056*
C12	0.4834 (3)	0.7399 (4)	1.0680 (2)	0.0414 (11)
H12A	0.5227	0.7949	1.0445	0.062*
H12B	0.5224	0.6943	1.1048	0.062*
H12C	0.4365	0.7840	1.0910	0.062*
C13	0.3303 (3)	0.2713 (3)	0.7337 (2)	0.0281 (8)
H13	0.3377	0.2342	0.7799	0.034*
C14	0.3642 (3)	0.2141 (4)	0.6759 (2)	0.0339 (9)
H14	0.3938	0.1396	0.6826	0.041*
C15	0.3541 (3)	0.2673 (4)	0.6086 (2)	0.0348 (9)
H15	0.3756	0.2287	0.5684	0.042*
C16	0.3124 (3)	0.3781 (4)	0.5999 (2)	0.0294 (8)
C17	0.3004 (3)	0.4407 (4)	0.5331 (2)	0.0364 (10)
H17	0.3221	0.4066	0.4914	0.044*
C18	0.2589 (3)	0.5477 (4)	0.5277 (2)	0.0368 (10)
H18	0.2539	0.5885	0.4828	0.044*
C19	0.2221 (3)	0.6008 (3)	0.5885 (2)	0.0289 (8)
C20	0.1742 (3)	0.7084 (4)	0.5857 (2)	0.0330 (9)
H20	0.1650	0.7516	0.5416	0.040*
C21	0.1407 (3)	0.7509 (4)	0.6463 (2)	0.0332 (9)
H21	0.1074	0.8232	0.6447	0.040*
C22	0.1561 (3)	0.6863 (3)	0.7115 (2)	0.0298 (8)
H22	0.1325	0.7163	0.7534	0.036*
C23	0.2340 (2)	0.5408 (3)	0.6556 (2)	0.0243 (8)
C24	0.2792 (3)	0.4293 (3)	0.6611 (2)	0.0247 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0266 (3)	0.0216 (2)	0.0211 (2)	0.00100 (18)	0.00519 (19)	0.00161 (18)
S1	0.0291 (5)	0.0380 (6)	0.0295 (5)	−0.0018 (4)	0.0000 (4)	0.0077 (4)
S2	0.0263 (5)	0.0313 (5)	0.0265 (5)	0.0023 (4)	0.0044 (4)	0.0068 (4)
S3	0.0307 (5)	0.0288 (5)	0.0274 (5)	0.0008 (4)	0.0091 (4)	−0.0011 (4)
S4	0.0278 (5)	0.0250 (5)	0.0312 (5)	−0.0001 (4)	0.0076 (4)	−0.0039 (4)
P1	0.0283 (5)	0.0246 (5)	0.0250 (5)	−0.0037 (4)	0.0047 (4)	0.0017 (4)
P2	0.0313 (5)	0.0224 (5)	0.0232 (5)	0.0003 (4)	0.0053 (4)	−0.0005 (4)
O1	0.0437 (17)	0.0279 (15)	0.0349 (16)	−0.0065 (12)	0.0112 (13)	−0.0006 (12)
O2	0.0291 (14)	0.0380 (16)	0.0260 (14)	0.0010 (12)	0.0059 (11)	0.0023 (12)
O3	0.0329 (14)	0.0237 (13)	0.0326 (15)	0.0012 (11)	0.0073 (12)	0.0044 (11)
O4	0.0393 (15)	0.0249 (14)	0.0272 (14)	0.0010 (12)	0.0008 (12)	−0.0025 (11)
N1	0.0252 (15)	0.0241 (16)	0.0224 (16)	0.0006 (12)	0.0029 (12)	0.0001 (12)
N2	0.0251 (16)	0.0261 (16)	0.0213 (15)	0.0016 (13)	0.0039 (12)	0.0018 (13)
C1	0.063 (3)	0.032 (2)	0.048 (3)	−0.004 (2)	0.018 (2)	−0.006 (2)
C2	0.068 (4)	0.065 (4)	0.048 (3)	−0.025 (3)	0.018 (3)	−0.017 (3)
C3	0.092 (4)	0.036 (3)	0.051 (3)	−0.024 (3)	0.011 (3)	0.000 (2)
C4	0.034 (2)	0.038 (2)	0.027 (2)	0.0034 (18)	0.0068 (17)	0.0028 (17)
C5	0.067 (3)	0.046 (3)	0.039 (3)	−0.004 (2)	0.006 (2)	−0.007 (2)
C6	0.089 (4)	0.064 (4)	0.041 (3)	−0.023 (3)	0.026 (3)	0.004 (3)
C7	0.036 (2)	0.029 (2)	0.037 (2)	−0.0024 (17)	0.0099 (18)	0.0031 (18)
C8	0.067 (3)	0.064 (3)	0.039 (3)	−0.017 (3)	0.016 (3)	0.009 (2)
C9	0.062 (3)	0.036 (3)	0.063 (3)	−0.014 (2)	0.015 (3)	−0.009 (2)
C10	0.036 (2)	0.035 (2)	0.028 (2)	0.0071 (18)	0.0023 (17)	0.0012 (17)
C11	0.041 (2)	0.036 (2)	0.032 (2)	0.0004 (19)	−0.0039 (18)	0.0046 (18)
C12	0.037 (2)	0.052 (3)	0.034 (2)	−0.006 (2)	−0.0028 (19)	−0.006 (2)
C13	0.030 (2)	0.0223 (18)	0.031 (2)	0.0022 (15)	0.0009 (16)	−0.0008 (16)
C14	0.036 (2)	0.027 (2)	0.040 (2)	0.0017 (17)	0.0108 (19)	−0.0024 (18)
C15	0.038 (2)	0.034 (2)	0.034 (2)	−0.0048 (18)	0.0116 (18)	−0.0107 (18)
C16	0.029 (2)	0.034 (2)	0.027 (2)	−0.0064 (16)	0.0094 (16)	−0.0063 (17)
C17	0.045 (2)	0.042 (2)	0.024 (2)	−0.007 (2)	0.0113 (18)	−0.0049 (18)
C18	0.049 (3)	0.037 (2)	0.024 (2)	−0.011 (2)	0.0056 (18)	0.0033 (17)
C19	0.033 (2)	0.029 (2)	0.0244 (19)	−0.0080 (16)	0.0025 (16)	0.0002 (16)
C20	0.036 (2)	0.032 (2)	0.030 (2)	−0.0012 (17)	0.0005 (17)	0.0104 (17)
C21	0.034 (2)	0.027 (2)	0.038 (2)	0.0026 (16)	0.0012 (18)	0.0078 (17)
C22	0.032 (2)	0.027 (2)	0.032 (2)	0.0008 (16)	0.0068 (17)	0.0028 (16)
C23	0.0196 (17)	0.0293 (19)	0.0239 (19)	−0.0040 (14)	0.0018 (14)	0.0031 (15)
C24	0.0242 (18)	0.0262 (19)	0.0240 (19)	−0.0055 (15)	0.0039 (15)	−0.0022 (15)

Geometric parameters (Å, º)

Ni—S1	2.4674 (11)	C6—H6C	0.9800
Ni—S2	2.4992 (11)	C7—C9	1.504 (6)
Ni—S3	2.4967 (11)	C7—C8	1.504 (6)
Ni—S4	2.5075 (11)	C7—H7	1.0000
Ni—N2	2.098 (3)	C8—H8A	0.9800
Ni—N1	2.100 (3)	C8—H8B	0.9800
S1—P1	1.9777 (14)	C8—H8C	0.9800
S2—P1	1.9880 (14)	C9—H9A	0.9800
S3—P2	1.9741 (14)	C9—H9B	0.9800
S4—P2	1.9947 (14)	C9—H9C	0.9800
P1—O2	1.586 (3)	C10—C11	1.505 (6)
P1—O1	1.584 (3)	C10—C12	1.515 (6)
P2—O3	1.594 (3)	C10—H10	1.0000
P2—O4	1.593 (3)	C11—H11A	0.9800
O1—C1	1.442 (5)	C11—H11B	0.9800
O2—C4	1.468 (5)	C11—H11C	0.9800
O3—C7	1.475 (5)	C12—H12A	0.9800
O4—C10	1.453 (5)	C12—H12B	0.9800
N1—C13	1.326 (5)	C12—H12C	0.9800
N1—C24	1.367 (5)	C13—C14	1.393 (6)
N2—C22	1.318 (5)	C13—H13	0.9500
N2—C23	1.369 (5)	C14—C15	1.380 (6)
C1—C2	1.470 (7)	C14—H14	0.9500
C1—C3	1.523 (7)	C15—C16	1.397 (6)
C1—H1	1.0000	C15—H15	0.9500
C2—H2A	0.9800	C16—C24	1.410 (5)
C2—H2B	0.9800	C16—C17	1.424 (6)
C2—H2C	0.9800	C17—C18	1.354 (6)
C3—H3A	0.9800	C17—H17	0.9500
C3—H3B	0.9800	C18—C19	1.437 (6)
C3—H3C	0.9800	C18—H18	0.9500
C4—C6	1.501 (6)	C19—C20	1.402 (6)
C4—C5	1.507 (6)	C19—C23	1.413 (5)
C4—H4	1.0000	C20—C21	1.366 (6)
C5—H5A	0.9800	C20—H20	0.9500
C5—H5B	0.9800	C21—C22	1.412 (6)
C5—H5C	0.9800	C21—H21	0.9500
C6—H6A	0.9800	C22—H22	0.9500
C6—H6B	0.9800	C23—C24	1.423 (5)
N2—Ni—N1	79.75 (12)	H6A—C6—H6C	109.5
N2—Ni—S1	92.01 (9)	H6B—C6—H6C	109.5
N1—Ni—S1	96.48 (9)	O3—C7—C9	107.8 (4)
N2—Ni—S3	93.50 (9)	O3—C7—C8	106.5 (4)
N1—Ni—S3	168.26 (9)	C9—C7—C8	114.1 (4)
S1—Ni—S3	93.33 (4)	O3—C7—H7	109.5
N2—Ni—S2	169.83 (9)	C9—C7—H7	109.5
N1—Ni—S2	92.88 (9)	C8—C7—H7	109.5
S1—Ni—S2	81.80 (4)	C7—C8—H8A	109.5
S3—Ni—S2	94.90 (4)	C7—C8—H8B	109.5
N2—Ni—S4	93.41 (9)	H8A—C8—H8B	109.5
N1—Ni—S4	89.14 (9)	C7—C8—H8C	109.5
S1—Ni—S4	172.81 (4)	H8A—C8—H8C	109.5
S3—Ni—S4	81.63 (3)	H8B—C8—H8C	109.5
S2—Ni—S4	93.48 (4)	C7—C9—H9A	109.5
P1—S1—Ni	83.09 (5)	C7—C9—H9B	109.5
P1—S2—Ni	82.06 (4)	H9A—C9—H9B	109.5
P2—S3—Ni	82.96 (4)	C7—C9—H9C	109.5
P2—S4—Ni	82.28 (5)	H9A—C9—H9C	109.5
O2—P1—O1	99.81 (15)	H9B—C9—H9C	109.5
O2—P1—S1	107.94 (12)	O4—C10—C11	112.3 (3)
O1—P1—S1	112.75 (12)	O4—C10—C12	105.3 (3)
O2—P1—S2	112.24 (12)	C11—C10—C12	112.7 (4)
O1—P1—S2	113.45 (12)	O4—C10—H10	108.8
S1—P1—S2	110.16 (6)	C11—C10—H10	108.8
O3—P2—O4	99.43 (15)	C12—C10—H10	108.8
O3—P2—S3	107.43 (11)	C10—C11—H11A	109.5
O4—P2—S3	114.06 (12)	C10—C11—H11B	109.5
O3—P2—S4	112.56 (11)	H11A—C11—H11B	109.5
O4—P2—S4	111.79 (12)	C10—C11—H11C	109.5
S3—P2—S4	111.01 (6)	H11A—C11—H11C	109.5
C1—O1—P1	126.6 (3)	H11B—C11—H11C	109.5
C4—O2—P1	121.0 (2)	C10—C12—H12A	109.5
C7—O3—P2	119.0 (2)	C10—C12—H12B	109.5
C10—O4—P2	125.1 (2)	H12A—C12—H12B	109.5
C13—N1—C24	118.3 (3)	C10—C12—H12C	109.5
C13—N1—Ni	129.0 (3)	H12A—C12—H12C	109.5
C24—N1—Ni	112.6 (2)	H12B—C12—H12C	109.5
C22—N2—C23	118.7 (3)	N1—C13—C14	123.0 (4)
C22—N2—Ni	129.0 (3)	N1—C13—H13	118.5
C23—N2—Ni	112.2 (2)	C14—C13—H13	118.5
O1—C1—C2	115.4 (4)	C15—C14—C13	119.1 (4)
O1—C1—C3	103.9 (4)	C15—C14—H14	120.5
C2—C1—C3	112.6 (4)	C13—C14—H14	120.5
O1—C1—H1	108.2	C14—C15—C16	119.8 (4)
C2—C1—H1	108.2	C14—C15—H15	120.1
C3—C1—H1	108.2	C16—C15—H15	120.1
C1—C2—H2A	109.5	C15—C16—C24	117.5 (4)
C1—C2—H2B	109.5	C15—C16—C17	123.8 (4)
H2A—C2—H2B	109.5	C24—C16—C17	118.7 (4)
C1—C2—H2C	109.5	C18—C17—C16	121.3 (4)
H2A—C2—H2C	109.5	C18—C17—H17	119.4
H2B—C2—H2C	109.5	C16—C17—H17	119.4
C1—C3—H3A	109.5	C17—C18—C19	121.3 (4)
C1—C3—H3B	109.5	C17—C18—H18	119.3
H3A—C3—H3B	109.5	C19—C18—H18	119.3
C1—C3—H3C	109.5	C20—C19—C23	117.5 (4)
H3A—C3—H3C	109.5	C20—C19—C18	124.2 (4)
H3B—C3—H3C	109.5	C23—C19—C18	118.3 (4)
O2—C4—C6	110.5 (4)	C21—C20—C19	119.8 (4)
O2—C4—C5	106.6 (3)	C21—C20—H20	120.1
C6—C4—C5	113.8 (4)	C19—C20—H20	120.1
O2—C4—H4	108.6	C20—C21—C22	119.3 (4)
C6—C4—H4	108.6	C20—C21—H21	120.3
C5—C4—H4	108.6	C22—C21—H21	120.3
C4—C5—H5A	109.5	N2—C22—C21	122.5 (4)
C4—C5—H5B	109.5	N2—C22—H22	118.8
H5A—C5—H5B	109.5	C21—C22—H22	118.8
C4—C5—H5C	109.5	N2—C23—C19	122.1 (3)
H5A—C5—H5C	109.5	N2—C23—C24	118.0 (3)
H5B—C5—H5C	109.5	C19—C23—C24	119.9 (3)
C4—C6—H6A	109.5	N1—C24—C16	122.3 (3)
C4—C6—H6B	109.5	N1—C24—C23	117.3 (3)
H6A—C6—H6B	109.5	C16—C24—C23	120.4 (3)
C4—C6—H6C	109.5
N2—Ni—S1—P1	−176.93 (9)	S3—Ni—N2—C22	−13.2 (3)
N1—Ni—S1—P1	103.16 (9)	S2—Ni—N2—C22	132.5 (4)
S3—Ni—S1—P1	−83.31 (5)	S4—Ni—N2—C22	−95.0 (3)
S2—Ni—S1—P1	11.17 (5)	N1—Ni—N2—C23	−4.0 (2)
N2—Ni—S2—P1	−64.1 (5)	S1—Ni—N2—C23	−100.2 (2)
N1—Ni—S2—P1	−107.28 (9)	S3—Ni—N2—C23	166.3 (2)
S1—Ni—S2—P1	−11.14 (5)	S2—Ni—N2—C23	−48.0 (6)
S3—Ni—S2—P1	81.52 (5)	S4—Ni—N2—C23	84.5 (2)
S4—Ni—S2—P1	163.41 (5)	P1—O1—C1—C2	−60.3 (6)
N2—Ni—S3—P2	−83.39 (9)	P1—O1—C1—C3	175.9 (3)
N1—Ni—S3—P2	−29.0 (4)	P1—O2—C4—C6	−101.8 (4)
S1—Ni—S3—P2	−175.61 (5)	P1—O2—C4—C5	134.1 (3)
S2—Ni—S3—P2	102.35 (5)	P2—O3—C7—C9	−115.4 (4)
S4—Ni—S3—P2	9.55 (4)	P2—O3—C7—C8	121.8 (3)
N2—Ni—S4—P2	83.57 (9)	P2—O4—C10—C11	−62.7 (4)
N1—Ni—S4—P2	163.25 (9)	P2—O4—C10—C12	174.4 (3)
S3—Ni—S4—P2	−9.46 (4)	C24—N1—C13—C14	−1.4 (6)
S2—Ni—S4—P2	−103.91 (5)	Ni—N1—C13—C14	−177.4 (3)
Ni—S1—P1—O2	107.99 (12)	N1—C13—C14—C15	0.3 (6)
Ni—S1—P1—O1	−142.74 (13)	C13—C14—C15—C16	1.5 (6)
Ni—S1—P1—S2	−14.89 (6)	C14—C15—C16—C24	−2.1 (6)
Ni—S2—P1—O2	−105.58 (12)	C14—C15—C16—C17	178.9 (4)
Ni—S2—P1—O1	142.20 (13)	C15—C16—C17—C18	179.6 (4)
Ni—S2—P1—S1	14.73 (6)	C24—C16—C17—C18	0.5 (6)
Ni—S3—P2—O3	110.69 (12)	C16—C17—C18—C19	−2.2 (6)
Ni—S3—P2—O4	−140.14 (12)	C17—C18—C19—C20	−176.7 (4)
Ni—S3—P2—S4	−12.77 (6)	C17—C18—C19—C23	2.8 (6)
Ni—S4—P2—O3	−107.73 (12)	C23—C19—C20—C21	−0.3 (6)
Ni—S4—P2—O4	141.33 (12)	C18—C19—C20—C21	179.1 (4)
Ni—S4—P2—S3	12.73 (6)	C19—C20—C21—C22	0.9 (6)
O2—P1—O1—C1	−163.2 (4)	C23—N2—C22—C21	−1.8 (6)
S1—P1—O1—C1	82.5 (4)	Ni—N2—C22—C21	177.7 (3)
S2—P1—O1—C1	−43.6 (4)	C20—C21—C22—N2	0.2 (6)
O1—P1—O2—C4	74.1 (3)	C22—N2—C23—C19	2.3 (5)
S1—P1—O2—C4	−168.0 (3)	Ni—N2—C23—C19	−177.2 (3)
S2—P1—O2—C4	−46.4 (3)	C22—N2—C23—C24	−176.8 (3)
O4—P2—O3—C7	68.5 (3)	Ni—N2—C23—C24	3.6 (4)
S3—P2—O3—C7	−172.5 (2)	C20—C19—C23—N2	−1.3 (5)
S4—P2—O3—C7	−50.0 (3)	C18—C19—C23—N2	179.2 (3)
O3—P2—O4—C10	−160.8 (3)	C20—C19—C23—C24	177.8 (3)
S3—P2—O4—C10	85.2 (3)	C18—C19—C23—C24	−1.7 (5)
S4—P2—O4—C10	−41.8 (3)	C13—N1—C24—C16	0.7 (5)
N2—Ni—N1—C13	−180.0 (3)	Ni—N1—C24—C16	177.3 (3)
S1—Ni—N1—C13	−89.1 (3)	C13—N1—C24—C23	−179.8 (3)
S3—Ni—N1—C13	124.4 (4)	Ni—N1—C24—C23	−3.1 (4)
S2—Ni—N1—C13	−7.0 (3)	C15—C16—C24—N1	1.0 (5)
S4—Ni—N1—C13	86.4 (3)	C17—C16—C24—N1	−179.9 (4)
N2—Ni—N1—C24	3.8 (2)	C15—C16—C24—C23	−178.5 (3)
S1—Ni—N1—C24	94.7 (2)	C17—C16—C24—C23	0.6 (5)
S3—Ni—N1—C24	−51.7 (6)	N2—C23—C24—N1	−0.3 (5)
S2—Ni—N1—C24	176.8 (2)	C19—C23—C24—N1	−179.5 (3)
S4—Ni—N1—C24	−89.8 (2)	N2—C23—C24—C16	179.2 (3)
N1—Ni—N2—C22	176.5 (3)	C19—C23—C24—C16	0.1 (5)
S1—Ni—N2—C22	80.3 (3)