(5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetra-aza-cyclo-tetra-deca-4,11-diene)nickel(II) bis-[O,O'-bis-(4-tert-butyl-phen-yl) dithio-phosphate].

The title salt, [Ni(C(16)H(32)N(4))](C(20)H(26)O(2)PS(2))(2), comprises a centrosymmetric [Ni(Me(6)[14]dieneN(4))](2+) dication (Me(6)[14]dieneN(4) is 5,7,7,12,14,14-hexa-methyl-1,4,8,11-tetra-aza-cyclo-tetra-deca-4,11-diene) and two O,O'-bis-(4-tert-butyl-phen-yl) dithio-phosphate anions. The Ni(II) ion lies on an inversion centre and displays a slightly distorted NiN(4) square-planar chelation arrangement with four N atoms from the Me(6)[14]dieneN(4) macrocycle. Two S atoms from symmetry-related anions are located in pseudo-axial positions with respect to the Ni(II) ion, with Ni⋯S distances of 3.2991 (7) Å. Inter-molecular N-H⋯S and C-H⋯S hydrogen bonds link the complex cation and pair of anions into a 1:2 type salt.

Related literature

For synthetic procedures, see: Li & Xie (1997 ▶); Xie et al. (2009 ▶). For applications as mimetic enzymes of transition metal complexes of tetra­mine macrocycles, see: Aoki & Kimura (2002 ▶). For related structures, see: Feng et al. (2010 ▶); He et al. (2010 ▶); Zou et al. (2010 ▶).

Experimental

Crystal data

[Ni(C16H32N4)](C20H26O2PS2)2

M = 1126.16

Triclinic,

a = 9.445 (2) Å

b = 12.168 (3) Å

c = 12.740 (3) Å

α = 95.965 (4)°

β = 91.360 (3)°

γ = 99.787 (4)°

V = 1433.7 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.59 mm−1

T = 103 K

0.27 × 0.23 × 0.08 mm

Data collection

Rigaku SPIDER diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.859, T max = 0.955

14032 measured reflections

6434 independent reflections

4838 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.101

S = 1.00

6434 reflections

335 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.35 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049615/pv2360sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049615/pv2360Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C16H32N4)](C20H26O2PS2)2	Z = 1
Mr = 1126.16	F(000) = 602
Triclinic, P1	Dx = 1.304 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.445 (2) Å	Cell parameters from 3818 reflections
b = 12.168 (3) Å	θ = 3.0–27.5°
c = 12.740 (3) Å	µ = 0.59 mm−1
α = 95.965 (4)°	T = 103 K
β = 91.360 (3)°	Plate, orange
γ = 99.787 (4)°	0.27 × 0.23 × 0.08 mm
V = 1433.7 (5) Å3

Rigaku SPIDER diffractometer	6434 independent reflections
Radiation source: Rotating Anode	4838 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
Tmin = 0.859, Tmax = 0.955	k = −15→14
14032 measured reflections	l = −16→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.698P] where P = (Fo2 + 2Fc2)/3
6434 reflections	(Δ/σ)max = 0.001
335 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ni1	0.0000	0.5000	0.5000	0.01467 (11)
P1	0.38240 (6)	0.74491 (5)	0.59769 (5)	0.01291 (13)
S1	0.18719 (6)	0.75534 (5)	0.55415 (5)	0.01884 (14)
S2	0.41409 (6)	0.65477 (5)	0.71245 (4)	0.01634 (13)
O1	0.47162 (17)	0.69494 (13)	0.50147 (12)	0.0163 (3)
O2	0.46883 (16)	0.87255 (13)	0.62254 (12)	0.0161 (3)
N1	−0.11781 (19)	0.56640 (16)	0.59937 (15)	0.0147 (4)
N2	−0.1166 (2)	0.54850 (17)	0.39160 (15)	0.0147 (4)
C1	−0.2353 (2)	0.6077 (2)	0.54470 (19)	0.0186 (5)
H1A	−0.2638	0.6718	0.5885	0.022*
H1B	−0.3203	0.5474	0.5312	0.022*
C2	−0.1784 (2)	0.6437 (2)	0.44242 (18)	0.0180 (5)
H2A	−0.2568	0.6602	0.3969	0.022*
H2B	−0.1036	0.7118	0.4555	0.022*
C3	−0.0567 (2)	0.56507 (19)	0.28493 (18)	0.0158 (5)
C4	−0.0187 (2)	0.4525 (2)	0.24158 (18)	0.0180 (5)
H4A	−0.1058	0.3944	0.2416	0.022*
H4B	0.0075	0.4569	0.1672	0.022*
C5	0.1014 (2)	0.41448 (19)	0.29968 (19)	0.0168 (5)
C6	0.0743 (2)	0.6583 (2)	0.29262 (18)	0.0172 (5)
H6A	0.0457	0.7298	0.3179	0.021*
H6B	0.1147	0.6633	0.2228	0.021*
H6C	0.1468	0.6417	0.3421	0.021*
C7	−0.1720 (2)	0.5932 (2)	0.20931 (18)	0.0176 (5)
H7A	−0.2588	0.5359	0.2077	0.021*
H7B	−0.1351	0.5950	0.1381	0.021*
H7C	−0.1954	0.6668	0.2341	0.021*
C8	0.1938 (3)	0.3504 (2)	0.2313 (2)	0.0233 (5)
H8A	0.2953	0.3819	0.2480	0.028*
H8B	0.1710	0.3562	0.1568	0.028*
H8C	0.1753	0.2714	0.2444	0.028*
C9	0.4542 (2)	0.70913 (19)	0.39500 (17)	0.0135 (4)
C10	0.4612 (2)	0.61550 (19)	0.32408 (18)	0.0148 (5)
H10	0.4730	0.5466	0.3492	0.018*
C11	0.4510 (2)	0.62328 (19)	0.21665 (18)	0.0153 (5)
H11	0.4557	0.5590	0.1685	0.018*
C12	0.4338 (2)	0.72341 (19)	0.17723 (18)	0.0155 (5)
C13	0.4277 (2)	0.81515 (19)	0.25037 (18)	0.0167 (5)
H13	0.4161	0.8842	0.2256	0.020*
C14	0.4379 (2)	0.80954 (19)	0.35900 (18)	0.0165 (5)
H14	0.4337	0.8737	0.4074	0.020*
C15	0.4216 (3)	0.7279 (2)	0.05768 (18)	0.0190 (5)
C16	0.5521 (3)	0.6889 (2)	0.00546 (19)	0.0248 (6)
H16A	0.5442	0.6924	−0.0709	0.030*
H16B	0.5550	0.6115	0.0192	0.030*
H16C	0.6404	0.7379	0.0348	0.030*
C17	0.4152 (3)	0.8452 (2)	0.0292 (2)	0.0342 (7)
H17A	0.4071	0.8437	−0.0478	0.041*
H17B	0.5030	0.8962	0.0564	0.041*
H17C	0.3315	0.8712	0.0606	0.041*
C18	0.2848 (3)	0.6490 (3)	0.0122 (2)	0.0341 (7)
H18A	0.2004	0.6748	0.0428	0.041*
H18B	0.2877	0.5728	0.0295	0.041*
H18C	0.2790	0.6491	−0.0647	0.041*
C19	0.6129 (2)	0.89734 (18)	0.65979 (18)	0.0155 (5)
C20	0.6442 (2)	0.90526 (19)	0.76688 (18)	0.0151 (5)
H20	0.5700	0.8875	0.8145	0.018*
C21	0.7862 (2)	0.93967 (19)	0.80414 (18)	0.0162 (5)
H21	0.8080	0.9446	0.8778	0.019*
C22	0.8978 (2)	0.96726 (19)	0.73619 (18)	0.0167 (5)
C23	0.8612 (3)	0.9561 (2)	0.62884 (19)	0.0220 (5)
H23	0.9349	0.9724	0.5804	0.026*
C24	0.7195 (3)	0.9215 (2)	0.59016 (19)	0.0208 (5)
H24	0.6970	0.9148	0.5164	0.025*
C25	1.0515 (2)	1.0085 (2)	0.78141 (19)	0.0192 (5)
C26	1.1533 (3)	1.0529 (2)	0.6975 (2)	0.0265 (6)
H26A	1.1627	0.9913	0.6436	0.032*
H26B	1.2479	1.0848	0.7308	0.032*
H26C	1.1142	1.1111	0.6643	0.032*
C27	1.0506 (3)	1.1031 (2)	0.8708 (2)	0.0261 (6)
H27A	1.0100	1.1640	0.8436	0.031*
H27B	1.1492	1.1317	0.8984	0.031*
H27C	0.9919	1.0741	0.9276	0.031*
C28	1.1095 (3)	0.9114 (2)	0.8255 (2)	0.0258 (6)
H28A	1.0468	0.8826	0.8803	0.031*
H28B	1.2070	0.9383	0.8560	0.031*
H28C	1.1117	0.8513	0.7684	0.031*
H2N	−0.185 (3)	0.490 (3)	0.379 (2)	0.046 (10)*

	U11	U22	U33	U12	U13	U23
Ni1	0.0110 (2)	0.0202 (2)	0.0153 (2)	0.00699 (16)	0.00251 (16)	0.00626 (17)
P1	0.0122 (3)	0.0134 (3)	0.0131 (3)	0.0027 (2)	0.0002 (2)	0.0005 (2)
S1	0.0125 (3)	0.0244 (3)	0.0195 (3)	0.0046 (2)	−0.0016 (2)	0.0007 (2)
S2	0.0169 (3)	0.0166 (3)	0.0154 (3)	0.0011 (2)	−0.0002 (2)	0.0047 (2)
O1	0.0179 (8)	0.0211 (9)	0.0119 (8)	0.0091 (6)	0.0002 (6)	0.0024 (7)
O2	0.0155 (8)	0.0124 (8)	0.0199 (9)	0.0017 (6)	−0.0031 (7)	0.0018 (7)
N1	0.0100 (9)	0.0168 (10)	0.0182 (10)	0.0036 (7)	0.0015 (7)	0.0045 (8)
N2	0.0113 (9)	0.0162 (10)	0.0185 (10)	0.0045 (7)	0.0029 (8)	0.0064 (8)
C1	0.0118 (11)	0.0243 (13)	0.0225 (13)	0.0089 (9)	0.0019 (9)	0.0062 (10)
C2	0.0159 (11)	0.0198 (12)	0.0204 (12)	0.0089 (9)	0.0018 (9)	0.0033 (10)
C3	0.0126 (11)	0.0187 (12)	0.0169 (12)	0.0027 (8)	0.0019 (9)	0.0059 (9)
C4	0.0148 (11)	0.0220 (12)	0.0167 (12)	0.0028 (9)	−0.0010 (9)	0.0012 (10)
C5	0.0113 (11)	0.0167 (12)	0.0217 (12)	0.0002 (8)	0.0015 (9)	0.0031 (10)
C6	0.0137 (11)	0.0225 (12)	0.0157 (12)	0.0017 (9)	0.0006 (9)	0.0055 (10)
C7	0.0144 (11)	0.0211 (12)	0.0184 (12)	0.0038 (9)	−0.0025 (9)	0.0074 (10)
C8	0.0204 (13)	0.0244 (13)	0.0251 (13)	0.0080 (10)	−0.0006 (10)	−0.0040 (11)
C9	0.0095 (10)	0.0197 (12)	0.0111 (11)	0.0022 (8)	0.0003 (8)	0.0016 (9)
C10	0.0122 (11)	0.0139 (11)	0.0185 (12)	0.0031 (8)	0.0022 (9)	0.0020 (9)
C11	0.0131 (11)	0.0153 (11)	0.0174 (12)	0.0034 (8)	0.0014 (9)	−0.0009 (9)
C12	0.0099 (10)	0.0211 (12)	0.0153 (11)	0.0026 (8)	0.0005 (8)	0.0011 (9)
C13	0.0186 (12)	0.0150 (11)	0.0168 (12)	0.0028 (9)	0.0005 (9)	0.0026 (9)
C14	0.0154 (11)	0.0167 (12)	0.0167 (12)	0.0023 (9)	−0.0008 (9)	−0.0005 (9)
C15	0.0185 (12)	0.0232 (13)	0.0157 (12)	0.0047 (9)	0.0004 (9)	0.0029 (10)
C16	0.0221 (13)	0.0367 (16)	0.0158 (12)	0.0057 (11)	0.0045 (10)	0.0017 (11)
C17	0.056 (2)	0.0365 (17)	0.0163 (13)	0.0209 (14)	0.0063 (13)	0.0094 (12)
C18	0.0226 (14)	0.060 (2)	0.0152 (13)	−0.0037 (13)	−0.0026 (11)	0.0036 (13)
C19	0.0134 (11)	0.0118 (11)	0.0208 (12)	0.0013 (8)	−0.0024 (9)	0.0013 (9)
C20	0.0175 (11)	0.0139 (11)	0.0141 (11)	0.0016 (8)	0.0041 (9)	0.0026 (9)
C21	0.0201 (12)	0.0180 (12)	0.0093 (11)	0.0007 (9)	0.0002 (9)	0.0004 (9)
C22	0.0162 (11)	0.0143 (11)	0.0189 (12)	−0.0003 (8)	0.0008 (9)	0.0036 (9)
C23	0.0187 (12)	0.0285 (14)	0.0164 (12)	−0.0029 (10)	0.0044 (10)	0.0019 (10)
C24	0.0231 (13)	0.0241 (13)	0.0135 (12)	−0.0012 (10)	−0.0013 (10)	0.0027 (10)
C25	0.0142 (11)	0.0217 (13)	0.0203 (12)	−0.0019 (9)	−0.0006 (9)	0.0039 (10)
C26	0.0156 (12)	0.0319 (15)	0.0289 (14)	−0.0044 (10)	0.0004 (10)	0.0033 (12)
C27	0.0246 (13)	0.0222 (14)	0.0261 (14)	−0.0069 (10)	−0.0025 (11)	−0.0036 (11)
C28	0.0201 (13)	0.0314 (15)	0.0266 (14)	0.0054 (10)	−0.0015 (11)	0.0061 (11)

Ni1—N1	1.9114 (19)	C11—C12	1.398 (3)
Ni1—N1i	1.9114 (19)	C11—H11	0.9500
Ni1—N2	1.9457 (19)	C12—C13	1.388 (3)
Ni1—N2i	1.9457 (19)	C12—C15	1.532 (3)
Ni1—S1	3.2990 (9)	C13—C14	1.394 (3)
P1—O2	1.6226 (16)	C13—H13	0.9500
P1—O1	1.6281 (17)	C14—H14	0.9500
P1—S1	1.9413 (9)	C15—C17	1.519 (4)
P1—S2	1.9632 (9)	C15—C18	1.534 (3)
O1—C9	1.394 (3)	C15—C16	1.536 (3)
O2—C19	1.403 (3)	C16—H16A	0.9800
N1—C5i	1.284 (3)	C16—H16B	0.9800
N1—C1	1.481 (3)	C16—H16C	0.9800
N2—C2	1.481 (3)	C17—H17A	0.9800
N2—C3	1.504 (3)	C17—H17B	0.9800
N2—H2N	0.88 (3)	C17—H17C	0.9800
C1—C2	1.500 (3)	C18—H18A	0.9800
C1—H1A	0.9900	C18—H18B	0.9800
C1—H1B	0.9900	C18—H18C	0.9800
C2—H2A	0.9900	C19—C24	1.372 (3)
C2—H2B	0.9900	C19—C20	1.379 (3)
C3—C6	1.524 (3)	C20—C21	1.392 (3)
C3—C4	1.526 (3)	C20—H20	0.9500
C3—C7	1.542 (3)	C21—C22	1.399 (3)
C4—C5	1.503 (3)	C21—H21	0.9500
C4—H4A	0.9900	C22—C23	1.390 (3)
C4—H4B	0.9900	C22—C25	1.531 (3)
C5—N1i	1.284 (3)	C23—C24	1.395 (3)
C5—C8	1.501 (3)	C23—H23	0.9500
C6—H6A	0.9800	C24—H24	0.9500
C6—H6B	0.9800	C25—C26	1.534 (3)
C6—H6C	0.9800	C25—C28	1.534 (4)
C7—H7A	0.9800	C25—C27	1.535 (3)
C7—H7B	0.9800	C26—H26A	0.9800
C7—H7C	0.9800	C26—H26B	0.9800
C8—H8A	0.9800	C26—H26C	0.9800
C8—H8B	0.9800	C27—H27A	0.9800
C8—H8C	0.9800	C27—H27B	0.9800
C9—C14	1.380 (3)	C27—H27C	0.9800
C9—C10	1.390 (3)	C28—H28A	0.9800
C10—C11	1.384 (3)	C28—H28B	0.9800
C10—H10	0.9500	C28—H28C	0.9800
N1—Ni1—N1i	180.0	C10—C11—C12	121.6 (2)
N1—Ni1—N2	86.13 (8)	C10—C11—H11	119.2
N1i—Ni1—N2	93.87 (8)	C12—C11—H11	119.2
N1—Ni1—N2i	93.87 (8)	C13—C12—C11	117.2 (2)
N1i—Ni1—N2i	86.13 (8)	C13—C12—C15	123.0 (2)
N2—Ni1—N2i	180.0	C11—C12—C15	119.8 (2)
N1—Ni1—S1	78.48 (6)	C12—C13—C14	122.3 (2)
N1i—Ni1—S1	101.52 (6)	C12—C13—H13	118.8
N2—Ni1—S1	91.63 (6)	C14—C13—H13	118.8
N2i—Ni1—S1	88.37 (6)	C9—C14—C13	118.8 (2)
O2—P1—O1	101.95 (9)	C9—C14—H14	120.6
O2—P1—S1	106.69 (7)	C13—C14—H14	120.6
O1—P1—S1	112.73 (6)	C17—C15—C12	112.5 (2)
O2—P1—S2	111.23 (6)	C17—C15—C18	108.5 (2)
O1—P1—S2	103.62 (7)	C12—C15—C18	109.3 (2)
S1—P1—S2	119.33 (4)	C17—C15—C16	108.0 (2)
P1—S1—Ni1	109.04 (3)	C12—C15—C16	109.77 (19)
C9—O1—P1	126.04 (15)	C18—C15—C16	108.7 (2)
C19—O2—P1	122.48 (14)	C15—C16—H16A	109.5
C5i—N1—C1	119.43 (19)	C15—C16—H16B	109.5
C5i—N1—Ni1	129.37 (16)	H16A—C16—H16B	109.5
C1—N1—Ni1	110.98 (14)	C15—C16—H16C	109.5
C2—N2—C3	115.10 (18)	H16A—C16—H16C	109.5
C2—N2—Ni1	106.77 (14)	H16B—C16—H16C	109.5
C3—N2—Ni1	119.71 (14)	C15—C17—H17A	109.5
C2—N2—H2N	109 (2)	C15—C17—H17B	109.5
C3—N2—H2N	104 (2)	H17A—C17—H17B	109.5
Ni1—N2—H2N	101 (2)	C15—C17—H17C	109.5
N1—C1—C2	106.80 (18)	H17A—C17—H17C	109.5
N1—C1—H1A	110.4	H17B—C17—H17C	109.5
C2—C1—H1A	110.4	C15—C18—H18A	109.5
N1—C1—H1B	110.4	C15—C18—H18B	109.5
C2—C1—H1B	110.4	H18A—C18—H18B	109.5
H1A—C1—H1B	108.6	C15—C18—H18C	109.5
N2—C2—C1	105.96 (19)	H18A—C18—H18C	109.5
N2—C2—H2A	110.5	H18B—C18—H18C	109.5
C1—C2—H2A	110.5	C24—C19—C20	121.0 (2)
N2—C2—H2B	110.5	C24—C19—O2	119.5 (2)
C1—C2—H2B	110.5	C20—C19—O2	119.3 (2)
H2A—C2—H2B	108.7	C19—C20—C21	119.0 (2)
N2—C3—C6	111.51 (19)	C19—C20—H20	120.5
N2—C3—C4	106.03 (19)	C21—C20—H20	120.5
C6—C3—C4	111.42 (19)	C20—C21—C22	121.9 (2)
N2—C3—C7	110.55 (18)	C20—C21—H21	119.1
C6—C3—C7	109.24 (19)	C22—C21—H21	119.1
C4—C3—C7	107.99 (18)	C23—C22—C21	116.9 (2)
C5—C4—C3	116.19 (19)	C23—C22—C25	123.1 (2)
C5—C4—H4A	108.2	C21—C22—C25	119.9 (2)
C3—C4—H4A	108.2	C22—C23—C24	121.9 (2)
C5—C4—H4B	108.2	C22—C23—H23	119.1
C3—C4—H4B	108.2	C24—C23—H23	119.1
H4A—C4—H4B	107.4	C19—C24—C23	119.3 (2)
N1i—C5—C8	124.0 (2)	C19—C24—H24	120.4
N1i—C5—C4	121.0 (2)	C23—C24—H24	120.4
C8—C5—C4	114.9 (2)	C22—C25—C26	112.07 (19)
C3—C6—H6A	109.5	C22—C25—C28	109.5 (2)
C3—C6—H6B	109.5	C26—C25—C28	108.1 (2)
H6A—C6—H6B	109.5	C22—C25—C27	109.1 (2)
C3—C6—H6C	109.5	C26—C25—C27	108.7 (2)
H6A—C6—H6C	109.5	C28—C25—C27	109.3 (2)
H6B—C6—H6C	109.5	C25—C26—H26A	109.5
C3—C7—H7A	109.5	C25—C26—H26B	109.5
C3—C7—H7B	109.5	H26A—C26—H26B	109.5
H7A—C7—H7B	109.5	C25—C26—H26C	109.5
C3—C7—H7C	109.5	H26A—C26—H26C	109.5
H7A—C7—H7C	109.5	H26B—C26—H26C	109.5
H7B—C7—H7C	109.5	C25—C27—H27A	109.5
C5—C8—H8A	109.5	C25—C27—H27B	109.5
C5—C8—H8B	109.5	H27A—C27—H27B	109.5
H8A—C8—H8B	109.5	C25—C27—H27C	109.5
C5—C8—H8C	109.5	H27A—C27—H27C	109.5
H8A—C8—H8C	109.5	H27B—C27—H27C	109.5
H8B—C8—H8C	109.5	C25—C28—H28A	109.5
C14—C9—C10	120.5 (2)	C25—C28—H28B	109.5
C14—C9—O1	123.8 (2)	H28A—C28—H28B	109.5
C10—C9—O1	115.6 (2)	C25—C28—H28C	109.5
C11—C10—C9	119.6 (2)	H28A—C28—H28C	109.5
C11—C10—H10	120.2	H28B—C28—H28C	109.5
C9—C10—H10	120.2
O2—P1—S1—Ni1	179.72 (6)	C3—C4—C5—N1i	36.6 (3)
O1—P1—S1—Ni1	68.62 (7)	C3—C4—C5—C8	−145.5 (2)
S2—P1—S1—Ni1	−53.26 (5)	P1—O1—C9—C14	42.9 (3)
N1—Ni1—S1—P1	126.44 (7)	P1—O1—C9—C10	−140.20 (18)
N1i—Ni1—S1—P1	−53.56 (7)	C14—C9—C10—C11	−0.3 (3)
N2—Ni1—S1—P1	−147.85 (6)	O1—C9—C10—C11	−177.36 (19)
N2i—Ni1—S1—P1	32.15 (6)	C9—C10—C11—C12	0.1 (3)
O2—P1—O1—C9	−82.29 (18)	C10—C11—C12—C13	0.1 (3)
S1—P1—O1—C9	31.73 (19)	C10—C11—C12—C15	−179.4 (2)
S2—P1—O1—C9	162.11 (15)	C11—C12—C13—C14	0.0 (3)
O1—P1—O2—C19	−63.81 (18)	C15—C12—C13—C14	179.5 (2)
S1—P1—O2—C19	177.78 (15)	C10—C9—C14—C13	0.4 (3)
S2—P1—O2—C19	46.09 (18)	O1—C9—C14—C13	177.2 (2)
N2—Ni1—N1—C5i	−169.7 (2)	C12—C13—C14—C9	−0.2 (3)
N2i—Ni1—N1—C5i	10.3 (2)	C13—C12—C15—C17	4.9 (3)
S1—Ni1—N1—C5i	−77.3 (2)	C11—C12—C15—C17	−175.5 (2)
N2—Ni1—N1—C1	4.72 (15)	C13—C12—C15—C18	−115.6 (3)
N2i—Ni1—N1—C1	−175.28 (15)	C11—C12—C15—C18	63.9 (3)
S1—Ni1—N1—C1	97.18 (14)	C13—C12—C15—C16	125.3 (2)
N1—Ni1—N2—C2	23.67 (14)	C11—C12—C15—C16	−55.2 (3)
N1i—Ni1—N2—C2	−156.33 (14)	P1—O2—C19—C24	98.6 (2)
S1—Ni1—N2—C2	−54.67 (14)	P1—O2—C19—C20	−86.2 (2)
N1—Ni1—N2—C3	156.67 (17)	C24—C19—C20—C21	0.8 (4)
N1i—Ni1—N2—C3	−23.33 (17)	O2—C19—C20—C21	−174.3 (2)
S1—Ni1—N2—C3	78.33 (16)	C19—C20—C21—C22	0.5 (4)
C5i—N1—C1—C2	143.3 (2)	C20—C21—C22—C23	−1.6 (4)
Ni1—N1—C1—C2	−31.7 (2)	C20—C21—C22—C25	177.9 (2)
C3—N2—C2—C1	178.12 (18)	C21—C22—C23—C24	1.5 (4)
Ni1—N2—C2—C1	−46.42 (19)	C25—C22—C23—C24	−178.0 (2)
N1—C1—C2—N2	50.7 (2)	C20—C19—C24—C23	−0.9 (4)
C2—N2—C3—C6	66.1 (2)	O2—C19—C24—C23	174.2 (2)
Ni1—N2—C3—C6	−63.2 (2)	C22—C23—C24—C19	−0.3 (4)
C2—N2—C3—C4	−172.42 (17)	C23—C22—C25—C26	9.1 (3)
Ni1—N2—C3—C4	58.2 (2)	C21—C22—C25—C26	−170.4 (2)
C2—N2—C3—C7	−55.6 (2)	C23—C22—C25—C28	−110.9 (3)
Ni1—N2—C3—C7	175.03 (14)	C21—C22—C25—C28	69.6 (3)
N2—C3—C4—C5	−66.3 (2)	C23—C22—C25—C27	129.5 (3)
C6—C3—C4—C5	55.2 (3)	C21—C22—C25—C27	−50.0 (3)
C7—C3—C4—C5	175.17 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S2i	0.88 (3)	2.70 (3)	3.542 (2)	162 (3)
C7—H7A···S2i	0.98	2.82	3.703 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯S2i	0.88 (3)	2.70 (3)	3.542 (2)	162 (3)
C7—H7A⋯S2i	0.98	2.82	3.703 (3)	150

Symmetry code: (i) .