(2,2′-Bipyrid­yl)bis­(O,O′-diisobutyl dithio­phosphato-κ²S,S′)nickel(II)

In the monomeric title compound,, [Ni(C₈H₁₈O₂PS₂)₂(C₁₀H₈N₂)], the Ni atom exhibits distorted octa­hedral N₂S₄ coordination. The crystal structure contains inter­molecular C—H...π and C—H...S inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 103 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.101
• Data-to-parameter ratio = 19.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.21 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.39 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    P2     -   O3      ..       5.03 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni     -   S1      ..       6.17 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni     -   S4      ..       5.33 su

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

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

---

Computing details

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.

(2,2'-Bipyridyl)bis(O,O'-diisobutyl dithiophosphato-κ²S,S')nickel(II)

Crystal data

[Ni(C8H18O2PS2)2(C10H8N2)]	F(000) = 1472
Mr = 697.52	Dx = 1.391 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 11956 reflections
a = 12.102 (2) Å	θ = 2.6–26.5°
b = 18.526 (3) Å	µ = 0.96 mm^−1
c = 15.307 (3) Å	T = 103 K
β = 103.954 (5)°	Plate, green
V = 3330.4 (10) Å^3	0.20 × 0.14 × 0.05 mm
Z = 4

Data collection

Rigaku AFC-12 κ /Saturn 224 CCD area-detector diffractometer	6854 independent reflections
Radiation source: fine-focus sealed tube	6441 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scans	θmax = 26.5°, θmin = 2.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −15→15
Tmin = 0.831, Tmax = 1.000	k = −23→23
61525 measured reflections	l = −19→19

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.038P)^2 + 5.4602P] where P = (Fo^2 + 2Fc^2)/3
6854 reflections	(Δ/σ)max = 0.001
352 parameters	Δρmax = 1.19 e Å^−3
0 restraints	Δρmin = −0.79 e Å^−3

Special details

Experimental. IR (KBr disk, cm^-1): ν(C—O) 1165, ν(P—O) 947, ν(P—S)_asymm 673, ν(P—S)_sym 560.

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	0.24986 (3)	0.280476 (16)	0.27651 (2)	0.01501 (9)
S1	0.35883 (5)	0.18621 (3)	0.37747 (4)	0.01871 (14)
S2	0.42337 (5)	0.28076 (3)	0.21743 (4)	0.02075 (14)
S3	0.07892 (6)	0.27027 (3)	0.33726 (5)	0.02431 (15)
S4	0.14111 (6)	0.18830 (3)	0.16869 (4)	0.02379 (15)
P1	0.46783 (5)	0.19838 (3)	0.30085 (4)	0.01726 (14)
P2	0.02093 (6)	0.20403 (4)	0.23563 (5)	0.02410 (16)
O1	0.59662 (15)	0.20359 (9)	0.35632 (13)	0.0247 (4)
O2	0.47529 (15)	0.12417 (9)	0.25003 (12)	0.0212 (4)
O3	−0.09807 (17)	0.23040 (10)	0.17497 (15)	0.0355 (5)
O4	−0.02850 (16)	0.13026 (10)	0.26322 (14)	0.0308 (5)
N2	0.30236 (17)	0.36658 (11)	0.36385 (14)	0.0174 (4)
N1	0.19217 (17)	0.36705 (10)	0.19276 (14)	0.0159 (4)
C1	0.6461 (2)	0.26921 (14)	0.40100 (18)	0.0234 (6)
H1A	0.6343	0.2712	0.4627	0.028*
H1B	0.6095	0.3120	0.3674	0.028*
C2	0.7726 (2)	0.26886 (15)	0.40453 (18)	0.0264 (6)
H2	0.7819	0.2702	0.3414	0.032*
C3	0.8249 (3)	0.33728 (19)	0.4523 (2)	0.0428 (8)
H3A	0.7860	0.3796	0.4206	0.064*
H3B	0.9059	0.3393	0.4527	0.064*
H3C	0.8164	0.3370	0.5144	0.064*
C4	0.8317 (2)	0.20175 (17)	0.4499 (2)	0.0314 (6)
H4A	0.7975	0.1589	0.4165	0.047*
H4B	0.8229	0.1992	0.5118	0.047*
H4C	0.9128	0.2038	0.4506	0.047*
C5	0.5516 (2)	0.12185 (15)	0.1894 (2)	0.0275 (6)
H5A	0.6313	0.1279	0.2243	0.033*
H5B	0.5332	0.1619	0.1454	0.033*
C6	0.5389 (2)	0.05085 (14)	0.14037 (19)	0.0259 (6)
H6	0.4577	0.0454	0.1063	0.031*
C7	0.6135 (3)	0.05342 (17)	0.0729 (2)	0.0331 (7)
H7A	0.6069	0.0077	0.0399	0.050*
H7B	0.6931	0.0611	0.1051	0.050*
H7C	0.5886	0.0931	0.0305	0.050*
C8	0.5699 (3)	−0.01240 (17)	0.2038 (3)	0.0475 (9)
H8A	0.5600	−0.0574	0.1692	0.071*
H8B	0.5204	−0.0129	0.2459	0.071*
H8C	0.6495	−0.0079	0.2375	0.071*
C9	−0.1089 (2)	0.30210 (15)	0.1358 (2)	0.0296 (6)
H9A	−0.0964	0.3000	0.0743	0.035*
H9B	−0.0506	0.3344	0.1726	0.035*
C10	−0.2256 (3)	0.33151 (16)	0.1322 (2)	0.0333 (7)
H10	−0.2320	0.3403	0.1952	0.040*
C11	−0.2377 (3)	0.40368 (17)	0.0828 (2)	0.0378 (7)
H11A	−0.1762	0.4361	0.1129	0.057*
H11B	−0.3113	0.4254	0.0835	0.057*
H11C	−0.2332	0.3960	0.0204	0.057*
C12	−0.3195 (3)	0.2799 (2)	0.0873 (3)	0.0518 (10)
H12A	−0.3101	0.2340	0.1200	0.078*
H12B	−0.3155	0.2715	0.0249	0.078*
H12C	−0.3936	0.3009	0.0879	0.078*
C13	0.0462 (2)	0.08078 (14)	0.3227 (2)	0.0284 (6)
H13A	0.0762	0.1037	0.3821	0.034*
H13B	0.1114	0.0679	0.2972	0.034*
C14	−0.0209 (2)	0.01355 (14)	0.33325 (18)	0.0232 (6)
H14	−0.0866	0.0281	0.3584	0.028*
C15	−0.0674 (3)	−0.02390 (16)	0.2435 (2)	0.0321 (6)
H15A	−0.1115	−0.0664	0.2527	0.048*
H15B	−0.0040	−0.0389	0.2181	0.048*
H15C	−0.1167	0.0095	0.2019	0.048*
C16	0.0555 (2)	−0.03722 (14)	0.40034 (19)	0.0259 (6)
H16A	0.0834	−0.0122	0.4578	0.039*
H16B	0.1202	−0.0522	0.3766	0.039*
H16C	0.0118	−0.0799	0.4096	0.039*
C17	0.1487 (2)	0.36337 (13)	0.10389 (17)	0.0190 (5)
H17	0.1383	0.3172	0.0761	0.023*
C18	0.1180 (2)	0.42393 (14)	0.05053 (18)	0.0215 (5)
H18	0.0888	0.4195	−0.0127	0.026*
C19	0.1309 (2)	0.49100 (13)	0.09150 (18)	0.0213 (5)
H19	0.1089	0.5335	0.0569	0.026*
C20	0.1762 (2)	0.49556 (13)	0.18328 (18)	0.0201 (5)
H20	0.1851	0.5411	0.2126	0.024*
C21	0.2086 (2)	0.43265 (12)	0.23229 (17)	0.0161 (5)
C22	0.2668 (2)	0.43233 (13)	0.32938 (17)	0.0170 (5)
C23	0.2878 (2)	0.49461 (13)	0.38114 (18)	0.0214 (5)
H23	0.2616	0.5401	0.3557	0.026*
C24	0.3472 (2)	0.48960 (14)	0.47036 (18)	0.0240 (6)
H24	0.3626	0.5316	0.5069	0.029*
C25	0.3839 (2)	0.42267 (15)	0.50545 (18)	0.0246 (6)
H25	0.4251	0.4179	0.5664	0.030*
C26	0.3597 (2)	0.36268 (14)	0.45017 (17)	0.0218 (5)
H26	0.3848	0.3167	0.4746	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.01763 (18)	0.01025 (15)	0.01638 (17)	0.00048 (11)	0.00259 (13)	0.00043 (11)
S1	0.0253 (3)	0.0132 (3)	0.0177 (3)	0.0027 (2)	0.0053 (3)	0.0018 (2)
S2	0.0216 (3)	0.0184 (3)	0.0233 (3)	0.0038 (2)	0.0075 (3)	0.0062 (2)
S3	0.0238 (3)	0.0201 (3)	0.0316 (4)	0.0006 (3)	0.0118 (3)	0.0025 (3)
S4	0.0321 (4)	0.0144 (3)	0.0220 (3)	−0.0028 (3)	0.0009 (3)	−0.0011 (2)
P1	0.0174 (3)	0.0129 (3)	0.0204 (3)	0.0011 (2)	0.0023 (3)	0.0006 (2)
P2	0.0193 (3)	0.0145 (3)	0.0343 (4)	−0.0014 (3)	−0.0018 (3)	0.0056 (3)
O1	0.0187 (9)	0.0156 (8)	0.0351 (11)	0.0002 (7)	−0.0027 (8)	0.0003 (8)
O2	0.0224 (9)	0.0158 (8)	0.0278 (10)	0.0000 (7)	0.0110 (8)	−0.0033 (7)
O3	0.0290 (11)	0.0194 (10)	0.0507 (13)	−0.0009 (8)	−0.0049 (10)	0.0086 (9)
O4	0.0195 (10)	0.0178 (9)	0.0492 (13)	−0.0016 (7)	−0.0032 (9)	0.0132 (9)
N2	0.0187 (11)	0.0139 (10)	0.0202 (10)	−0.0003 (8)	0.0059 (9)	−0.0004 (8)
N1	0.0149 (10)	0.0126 (9)	0.0207 (10)	0.0003 (7)	0.0052 (8)	0.0008 (8)
C1	0.0247 (14)	0.0178 (12)	0.0252 (13)	−0.0033 (10)	0.0014 (11)	−0.0029 (10)
C2	0.0263 (14)	0.0313 (15)	0.0221 (13)	−0.0073 (11)	0.0066 (11)	0.0023 (11)
C3	0.0332 (17)	0.0435 (19)	0.051 (2)	−0.0176 (14)	0.0084 (15)	−0.0095 (16)
C4	0.0197 (14)	0.0408 (17)	0.0330 (16)	−0.0004 (12)	0.0050 (12)	0.0054 (13)
C5	0.0291 (15)	0.0240 (14)	0.0341 (15)	−0.0012 (11)	0.0166 (13)	−0.0029 (12)
C6	0.0257 (14)	0.0237 (14)	0.0303 (14)	0.0030 (11)	0.0108 (12)	−0.0037 (11)
C7	0.0324 (16)	0.0378 (17)	0.0321 (16)	0.0074 (13)	0.0135 (13)	−0.0021 (13)
C8	0.063 (2)	0.0280 (16)	0.065 (2)	0.0168 (15)	0.042 (2)	0.0118 (16)
C9	0.0289 (15)	0.0251 (14)	0.0329 (15)	0.0016 (11)	0.0038 (13)	0.0075 (12)
C10	0.0347 (16)	0.0353 (16)	0.0326 (16)	0.0103 (13)	0.0135 (13)	0.0087 (13)
C11	0.0438 (19)	0.0351 (17)	0.0365 (17)	0.0140 (14)	0.0135 (15)	0.0108 (13)
C12	0.038 (2)	0.048 (2)	0.064 (2)	−0.0078 (16)	0.0025 (18)	0.0187 (18)
C13	0.0210 (14)	0.0188 (13)	0.0406 (16)	0.0000 (10)	−0.0022 (12)	0.0120 (12)
C14	0.0210 (13)	0.0181 (12)	0.0318 (14)	−0.0004 (10)	0.0088 (11)	0.0043 (11)
C15	0.0320 (16)	0.0252 (14)	0.0359 (16)	−0.0010 (12)	0.0018 (13)	0.0036 (12)
C16	0.0252 (14)	0.0220 (13)	0.0309 (14)	−0.0009 (11)	0.0075 (12)	0.0066 (11)
C17	0.0191 (13)	0.0167 (12)	0.0199 (12)	0.0002 (9)	0.0023 (10)	0.0006 (10)
C18	0.0182 (13)	0.0227 (13)	0.0222 (13)	0.0000 (10)	0.0021 (11)	0.0042 (10)
C19	0.0169 (12)	0.0174 (12)	0.0295 (14)	0.0037 (10)	0.0052 (11)	0.0077 (10)
C20	0.0181 (12)	0.0134 (11)	0.0294 (13)	0.0014 (9)	0.0068 (11)	0.0022 (10)
C21	0.0133 (11)	0.0134 (11)	0.0233 (12)	−0.0003 (9)	0.0076 (10)	0.0005 (9)
C22	0.0141 (12)	0.0140 (11)	0.0234 (13)	−0.0004 (9)	0.0054 (10)	0.0006 (9)
C23	0.0229 (13)	0.0131 (11)	0.0291 (14)	0.0007 (10)	0.0079 (11)	0.0000 (10)
C24	0.0259 (14)	0.0185 (12)	0.0283 (14)	−0.0026 (10)	0.0080 (12)	−0.0091 (11)
C25	0.0253 (14)	0.0255 (14)	0.0217 (13)	−0.0006 (11)	0.0029 (11)	−0.0047 (11)
C26	0.0247 (14)	0.0183 (12)	0.0207 (13)	0.0015 (10)	0.0017 (11)	−0.0008 (10)

Geometric parameters (Å, º)

Ni—S1	2.4888 (7)	C8—H8B	0.980
Ni—S2	2.4784 (8)	C8—H8C	0.980
Ni—S3	2.4715 (8)	C9—C10	1.501 (4)
Ni—S4	2.5148 (7)	C9—H9A	0.990
Ni—N1	2.067 (2)	C9—H9B	0.990
Ni—N2	2.080 (2)	C10—C12	1.517 (5)
S1—P1	1.9781 (9)	C10—C11	1.525 (4)
S2—P1	1.9793 (9)	C10—H10	1.000
S3—P2	1.9729 (10)	C11—H11A	0.980
S4—P2	1.9922 (11)	C11—H11B	0.980
P1—O1	1.5878 (19)	C11—H11C	0.980
P1—O2	1.5929 (18)	C12—H12A	0.980
P2—O4	1.5892 (19)	C12—H12B	0.980
P2—O3	1.591 (2)	C12—H12C	0.980
O1—C1	1.452 (3)	C13—C14	1.517 (3)
O2—C5	1.459 (3)	C13—H13A	0.990
O3—C9	1.450 (3)	C13—H13B	0.990
O4—C13	1.445 (3)	C14—C15	1.520 (4)
N2—C26	1.338 (3)	C14—C16	1.528 (4)
N2—C22	1.356 (3)	C14—H14	1.000
N1—C17	1.337 (3)	C15—H15A	0.980
N1—C21	1.351 (3)	C15—H15B	0.980
C1—C2	1.519 (4)	C15—H15C	0.980
C1—H1A	0.990	C16—H16A	0.980
C1—H1B	0.990	C16—H16B	0.980
C2—C4	1.516 (4)	C16—H16C	0.980
C2—C3	1.523 (4)	C17—C18	1.385 (3)
C2—H2	1.000	C17—H17	0.950
C3—H3A	0.980	C18—C19	1.384 (4)
C3—H3B	0.980	C18—H18	0.950
C3—H3C	0.980	C19—C20	1.382 (4)
C4—H4A	0.980	C19—H19	0.950
C4—H4B	0.980	C20—C21	1.390 (3)
C4—H4C	0.980	C20—H20	0.950
C5—C6	1.504 (4)	C21—C22	1.483 (3)
C5—H5A	0.990	C22—C23	1.388 (3)
C5—H5B	0.990	C23—C24	1.385 (4)
C6—C8	1.510 (4)	C23—H23	0.950
C6—C7	1.528 (4)	C24—C25	1.381 (4)
C6—H6	1.000	C24—H24	0.950
C7—H7A	0.980	C25—C26	1.385 (4)
C7—H7B	0.980	C25—H25	0.950
C7—H7C	0.980	C26—H26	0.950
C8—H8A	0.980
S1—Ni—S2	81.92 (2)	C6—C8—H8B	109.5
S1—Ni—S3	94.52 (3)	H8A—C8—H8B	109.5
S1—Ni—S4	92.64 (3)	C6—C8—H8C	109.5
S1—Ni—N1	168.19 (6)	H8A—C8—H8C	109.5
S1—Ni—N2	96.02 (6)	H8B—C8—H8C	109.5
S2—Ni—S3	175.67 (2)	O3—C9—C10	109.8 (2)
S2—Ni—S4	96.74 (3)	O3—C9—H9A	109.7
S2—Ni—N1	87.78 (6)	C10—C9—H9A	109.7
S2—Ni—N2	94.51 (6)	O3—C9—H9B	109.7
S3—Ni—S4	80.90 (3)	C10—C9—H9B	109.7
S3—Ni—N1	96.00 (6)	H9A—C9—H9B	108.2
S3—Ni—N2	88.31 (6)	C9—C10—C12	112.6 (3)
S4—Ni—N1	94.30 (6)	C9—C10—C11	108.3 (2)
S4—Ni—N2	166.66 (6)	C12—C10—C11	110.8 (3)
N1—Ni—N2	78.97 (8)	C9—C10—H10	108.3
P1—S1—Ni	83.17 (3)	C12—C10—H10	108.3
P1—S2—Ni	83.42 (3)	C11—C10—H10	108.3
P2—S3—Ni	85.51 (3)	C10—C11—H11A	109.5
P2—S4—Ni	83.95 (3)	C10—C11—H11B	109.5
O1—P1—O2	98.61 (10)	H11A—C11—H11B	109.5
O1—P1—S1	113.50 (8)	C10—C11—H11C	109.5
O2—P1—S1	108.40 (7)	H11A—C11—H11C	109.5
O1—P1—S2	112.16 (8)	H11B—C11—H11C	109.5
O2—P1—S2	112.89 (8)	C10—C12—H12A	109.5
S1—P1—S2	110.73 (4)	C10—C12—H12B	109.5
O4—P2—O3	94.22 (10)	H12A—C12—H12B	109.5
O4—P2—S3	114.23 (9)	C10—C12—H12C	109.5
O3—P2—S3	111.66 (9)	H12A—C12—H12C	109.5
O4—P2—S4	112.29 (9)	H12B—C12—H12C	109.5
O3—P2—S4	114.53 (10)	O4—C13—C14	108.6 (2)
S3—P2—S4	109.36 (4)	O4—C13—H13A	110.0
C1—O1—P1	122.91 (16)	C14—C13—H13A	110.0
C5—O2—P1	117.08 (15)	O4—C13—H13B	110.0
C9—O3—P2	120.12 (18)	C14—C13—H13B	110.0
C13—O4—P2	119.63 (16)	H13A—C13—H13B	108.4
C26—N2—C22	118.2 (2)	C13—C14—C15	111.7 (2)
C26—N2—Ni	126.78 (17)	C13—C14—C16	108.9 (2)
C22—N2—Ni	114.82 (16)	C15—C14—C16	111.0 (2)
C17—N1—C21	118.8 (2)	C13—C14—H14	108.4
C17—N1—Ni	125.65 (16)	C15—C14—H14	108.4
C21—N1—Ni	115.41 (16)	C16—C14—H14	108.4
O1—C1—C2	108.1 (2)	C14—C15—H15A	109.5
O1—C1—H1A	110.1	C14—C15—H15B	109.5
C2—C1—H1A	110.1	H15A—C15—H15B	109.5
O1—C1—H1B	110.1	C14—C15—H15C	109.5
C2—C1—H1B	110.1	H15A—C15—H15C	109.5
H1A—C1—H1B	108.4	H15B—C15—H15C	109.5
C4—C2—C1	112.3 (2)	C14—C16—H16A	109.5
C4—C2—C3	111.6 (3)	C14—C16—H16B	109.5
C1—C2—C3	108.2 (2)	H16A—C16—H16B	109.5
C4—C2—H2	108.2	C14—C16—H16C	109.5
C1—C2—H2	108.2	H16A—C16—H16C	109.5
C3—C2—H2	108.2	H16B—C16—H16C	109.5
C2—C3—H3A	109.5	N1—C17—C18	122.9 (2)
C2—C3—H3B	109.5	N1—C17—H17	118.6
H3A—C3—H3B	109.5	C18—C17—H17	118.6
C2—C3—H3C	109.5	C19—C18—C17	118.4 (2)
H3A—C3—H3C	109.5	C19—C18—H18	120.8
H3B—C3—H3C	109.5	C17—C18—H18	120.8
C2—C4—H4A	109.5	C20—C19—C18	119.3 (2)
C2—C4—H4B	109.5	C20—C19—H19	120.3
H4A—C4—H4B	109.5	C18—C19—H19	120.3
C2—C4—H4C	109.5	C19—C20—C21	119.2 (2)
H4A—C4—H4C	109.5	C19—C20—H20	120.4
H4B—C4—H4C	109.5	C21—C20—H20	120.4
O2—C5—C6	109.8 (2)	N1—C21—C20	121.4 (2)
O2—C5—H5A	109.7	N1—C21—C22	115.4 (2)
C6—C5—H5A	109.7	C20—C21—C22	123.2 (2)
O2—C5—H5B	109.7	N2—C22—C23	121.8 (2)
C6—C5—H5B	109.7	N2—C22—C21	115.0 (2)
H5A—C5—H5B	108.2	C23—C22—C21	123.1 (2)
C5—C6—C8	112.2 (3)	C24—C23—C22	119.2 (2)
C5—C6—C7	107.7 (2)	C24—C23—H23	120.4
C8—C6—C7	111.3 (2)	C22—C23—H23	120.4
C5—C6—H6	108.5	C25—C24—C23	119.1 (2)
C8—C6—H6	108.5	C25—C24—H24	120.5
C7—C6—H6	108.5	C23—C24—H24	120.5
C6—C7—H7A	109.5	C24—C25—C26	118.8 (2)
C6—C7—H7B	109.5	C24—C25—H25	120.6
H7A—C7—H7B	109.5	C26—C25—H25	120.6
C6—C7—H7C	109.5	N2—C26—C25	122.9 (2)
H7A—C7—H7C	109.5	N2—C26—H26	118.5
H7B—C7—H7C	109.5	C25—C26—H26	118.5
C6—C8—H8A	109.5
N1—Ni—S1—P1	−35.3 (3)	S1—Ni—N2—C22	174.89 (16)
N2—Ni—S1—P1	−99.46 (6)	S4—Ni—N2—C22	−54.9 (3)
S3—Ni—S1—P1	171.77 (3)	N2—Ni—N1—C17	171.6 (2)
S2—Ni—S1—P1	−5.74 (3)	S3—Ni—N1—C17	−101.28 (19)
S4—Ni—S1—P1	90.70 (3)	S2—Ni—N1—C17	76.60 (19)
N1—Ni—S2—P1	179.94 (6)	S1—Ni—N1—C17	105.8 (3)
N2—Ni—S2—P1	101.19 (6)	S4—Ni—N1—C17	−20.0 (2)
S1—Ni—S2—P1	5.73 (3)	N2—Ni—N1—C21	−3.37 (16)
S4—Ni—S2—P1	−85.99 (3)	S3—Ni—N1—C21	83.72 (16)
N1—Ni—S3—P2	89.95 (6)	S2—Ni—N1—C21	−98.40 (16)
N2—Ni—S3—P2	168.67 (6)	S1—Ni—N1—C21	−69.2 (4)
S1—Ni—S3—P2	−95.42 (3)	S4—Ni—N1—C21	165.01 (16)
S4—Ni—S3—P2	−3.46 (3)	P1—O1—C1—C2	−151.43 (18)
N1—Ni—S4—P2	−91.97 (6)	O1—C1—C2—C4	−55.8 (3)
N2—Ni—S4—P2	−33.0 (3)	O1—C1—C2—C3	−179.4 (2)
S3—Ni—S4—P2	3.44 (3)	P1—O2—C5—C6	−174.18 (18)
S2—Ni—S4—P2	179.76 (3)	O2—C5—C6—C8	−61.4 (3)
S1—Ni—S4—P2	97.60 (3)	O2—C5—C6—C7	175.8 (2)
Ni—S1—P1—O1	134.80 (8)	P2—O3—C9—C10	−145.9 (2)
Ni—S1—P1—O2	−116.73 (8)	O3—C9—C10—C12	−51.9 (3)
Ni—S1—P1—S2	7.62 (4)	O3—C9—C10—C11	−174.8 (2)
Ni—S2—P1—O1	−135.57 (8)	P2—O4—C13—C14	−176.71 (19)
Ni—S2—P1—O2	114.10 (8)	O4—C13—C14—C15	60.3 (3)
Ni—S2—P1—S1	−7.65 (4)	O4—C13—C14—C16	−176.7 (2)
Ni—S3—P2—O4	131.37 (8)	C21—N1—C17—C18	−1.0 (4)
Ni—S3—P2—O3	−123.24 (9)	Ni—N1—C17—C18	−175.84 (18)
Ni—S3—P2—S4	4.57 (4)	N1—C17—C18—C19	−1.4 (4)
Ni—S4—P2—O4	−132.40 (9)	C17—C18—C19—C20	1.5 (4)
Ni—S4—P2—O3	121.68 (9)	C18—C19—C20—C21	0.5 (4)
Ni—S4—P2—S3	−4.51 (4)	C17—N1—C21—C20	3.2 (3)
O2—P1—O1—C1	166.2 (2)	Ni—N1—C21—C20	178.54 (18)
S1—P1—O1—C1	−79.4 (2)	C17—N1—C21—C22	−174.7 (2)
S2—P1—O1—C1	47.1 (2)	Ni—N1—C21—C22	0.7 (3)
O1—P1—O2—C5	−61.8 (2)	C19—C20—C21—N1	−3.0 (4)
S1—P1—O2—C5	179.82 (16)	C19—C20—C21—C22	174.7 (2)
S2—P1—O2—C5	56.77 (19)	C26—N2—C22—C23	−0.4 (4)
O4—P2—O3—C9	174.1 (2)	Ni—N2—C22—C23	175.33 (18)
S3—P2—O3—C9	56.0 (2)	C26—N2—C22—C21	177.3 (2)
S4—P2—O3—C9	−69.0 (2)	Ni—N2—C22—C21	−7.0 (3)
O3—P2—O4—C13	−179.5 (2)	N1—C21—C22—N2	4.2 (3)
S3—P2—O4—C13	−63.4 (2)	C20—C21—C22—N2	−173.6 (2)
S4—P2—O4—C13	61.8 (2)	N1—C21—C22—C23	−178.2 (2)
N1—Ni—N2—C26	−179.0 (2)	C20—C21—C22—C23	4.1 (4)
S3—Ni—N2—C26	84.5 (2)	N2—C22—C23—C24	0.4 (4)
S2—Ni—N2—C26	−92.2 (2)	C21—C22—C23—C24	−177.1 (2)
S1—Ni—N2—C26	−9.8 (2)	C22—C23—C24—C25	−0.1 (4)
S4—Ni—N2—C26	120.4 (3)	C23—C24—C25—C26	−0.2 (4)
N1—Ni—N2—C22	5.71 (16)	C22—N2—C26—C25	0.1 (4)
S3—Ni—N2—C22	−90.74 (16)	Ni—N2—C26—C25	−175.1 (2)
S2—Ni—N2—C22	92.56 (16)	C24—C25—C26—N2	0.2 (4)