(meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetra-aza-cyclo-tetra-deca-ne)nickel(II) bis-[O,O'-bis-(4-methyl-phen-yl) thio-phosphate].

In the centrosymmetric title complex, [Ni(C(16)H(36)N(4))](C(14)H(14)O(3)PS)(2), the Ni(II) ion is coordinated by four N atoms and two O atoms within a slightly distorted NiN(4)O(2) octa-hedral geometry. The asymmetric unit consits of one Ni(II) ion that is located on a center of inversion, half of the macrocylic ligand and one anion occupying general positions. Intra-molecular N-H⋯O and N-H⋯S hydrogen bonding is found between the macrocyclic ligand and the monothio-phosphate anion.

Related literature

For the synthesis of O,O′-bis­(4-methyl­phen­yl) monothio­phos­phate, see: Pesin & Khaletakii (1961 ▶). For related structures, see: Feng et al. (2010 ▶); He et al. (2010 ▶); Zou et al. (2010 ▶).

Experimental

Crystal data

[Ni(C16H36N4)](C14H14O3PS)2

M = 929.76

Monoclinic,

a = 10.977 (2) Å

b = 16.360 (3) Å

c = 12.767 (3) Å

β = 94.85 (3)°

V = 2284.6 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.64 mm−1

T = 113 K

0.24 × 0.23 × 0.22 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.862, T max = 0.873

18654 measured reflections

5376 independent reflections

2665 reflections with I > 2σ(I)

R int = 0.101

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.122

S = 0.99

5376 reflections

281 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.97 e Å−3

Δρmin = −0.91 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536810051184/nc2207sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051184/nc2207Isup2.hkl

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

[Ni(C16H36N4)](C14H14O3PS)2	F(000) = 988
Mr = 929.76	Dx = 1.352 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7232 reflections
a = 10.977 (2) Å	θ = 2.2–27.9°
b = 16.360 (3) Å	µ = 0.64 mm−1
c = 12.767 (3) Å	T = 113 K
β = 94.85 (3)°	Block, orange
V = 2284.6 (8) Å3	0.24 × 0.23 × 0.22 mm
Z = 2

Rigaku Saturn CCD area-detector diffractometer	5376 independent reflections
Radiation source: rotating anode	2665 reflections with I > 2σ(I)
confocal	Rint = 0.101
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.2°
φ and ω scans	h = −14→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −21→19
Tmin = 0.862, Tmax = 0.873	l = −16→16
18654 measured reflections

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)] = 0.053	Hydrogen site location: mixed
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0244P)2] where P = (Fo2 + 2Fc2)/3
5376 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 0.97 e Å−3
0 restraints	Δρmin = −0.91 e Å−3

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.

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 > 2sigma(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	0.5000	0.5000	0.5000	0.02073 (17)
P1	0.49238 (7)	0.69655 (5)	0.59137 (7)	0.0216 (2)
S1	0.57082 (7)	0.69510 (5)	0.73310 (7)	0.0288 (2)
O1	0.38094 (17)	0.76174 (13)	0.58832 (18)	0.0236 (6)
O2	0.58179 (16)	0.73444 (12)	0.50834 (17)	0.0214 (5)
O3	0.44815 (16)	0.61948 (12)	0.53863 (17)	0.0223 (5)
N1	0.3899 (2)	0.50845 (17)	0.3600 (2)	0.0219 (6)
H1	0.395 (3)	0.4578 (19)	0.329 (3)	0.035 (10)*
N2	0.6334 (2)	0.55494 (16)	0.4156 (2)	0.0215 (7)
H2	0.616 (3)	0.6087 (18)	0.441 (3)	0.030 (9)*
C1	0.2889 (3)	0.76449 (19)	0.5047 (3)	0.0223 (8)
C2	0.3144 (3)	0.76956 (19)	0.4017 (3)	0.0246 (8)
H2A	0.3966	0.7682	0.3837	0.030*
C3	0.2189 (3)	0.7767 (2)	0.3242 (3)	0.0275 (8)
H3	0.2366	0.7805	0.2528	0.033*
C4	0.0970 (3)	0.77851 (19)	0.3485 (3)	0.0250 (8)
C5	0.0746 (3)	0.7723 (2)	0.4531 (3)	0.0278 (9)
H5	−0.0073	0.7727	0.4719	0.033*
C6	0.1699 (3)	0.7656 (2)	0.5310 (3)	0.0296 (9)
H6	0.1531	0.7617	0.6026	0.035*
C7	−0.0083 (3)	0.7901 (2)	0.2647 (3)	0.0389 (10)
H7A	−0.0184	0.7405	0.2218	0.058*
H7C	0.0093	0.8365	0.2198	0.058*
H7B	−0.0837	0.8009	0.2984	0.058*
C8	0.6458 (3)	0.80740 (19)	0.5269 (3)	0.0217 (8)
C9	0.7636 (3)	0.8040 (2)	0.5759 (3)	0.0267 (8)
H9	0.7978	0.7536	0.6008	0.032*
C10	0.8303 (3)	0.8763 (2)	0.5877 (3)	0.0307 (9)
H10	0.9115	0.8743	0.6199	0.037*
C11	0.7829 (3)	0.9500 (2)	0.5545 (3)	0.0295 (9)
C12	0.6644 (3)	0.9517 (2)	0.5073 (3)	0.0341 (9)
H12	0.6292	1.0023	0.4843	0.041*
C13	0.5966 (3)	0.8805 (2)	0.4934 (3)	0.0301 (9)
H13	0.5157	0.8826	0.4605	0.036*
C14	0.8567 (3)	1.0273 (2)	0.5677 (3)	0.0458 (11)
H14A	0.8793	1.0458	0.4989	0.069*
H14B	0.9310	1.0169	0.6139	0.069*
H14C	0.8080	1.0697	0.5989	0.069*
C15	0.8417 (3)	0.6094 (2)	0.3973 (3)	0.0361 (10)
H15A	0.8263	0.6104	0.3206	0.054*
H15C	0.9291	0.6010	0.4164	0.054*
H15B	0.8161	0.6615	0.4264	0.054*
C16	0.8058 (3)	0.45790 (19)	0.3946 (3)	0.0322 (9)
H16A	0.7479	0.4153	0.4115	0.048*
H16C	0.8882	0.4429	0.4239	0.048*
H16B	0.8050	0.4635	0.3182	0.048*
C17	0.7688 (3)	0.5393 (2)	0.4421 (3)	0.0264 (8)
C18	0.5894 (3)	0.5475 (2)	0.3036 (3)	0.0292 (9)
H18A	0.6039	0.4914	0.2783	0.035*
H18B	0.6335	0.5864	0.2610	0.035*
C19	0.4532 (3)	0.5665 (2)	0.2936 (3)	0.0286 (9)
H19B	0.4395	0.6233	0.3167	0.034*
H19A	0.4202	0.5612	0.2193	0.034*
C20	0.2599 (3)	0.5272 (2)	0.3719 (3)	0.0271 (8)
H20	0.2554	0.5804	0.4102	0.033*
C21	0.2064 (3)	0.4599 (2)	0.4382 (3)	0.0284 (9)
H21B	0.1166	0.4606	0.4221	0.034*
H21A	0.2360	0.4069	0.4129	0.034*
C22	0.1847 (3)	0.5349 (2)	0.2649 (3)	0.0393 (10)
H22C	0.2188	0.5788	0.2240	0.059*
H22B	0.0996	0.5477	0.2762	0.059*
H22A	0.1880	0.4832	0.2266	0.059*

	U11	U22	U33	U12	U13	U23
Ni1	0.0054 (3)	0.0286 (3)	0.0277 (4)	−0.0020 (2)	−0.0018 (2)	0.0003 (3)
P1	0.0101 (4)	0.0288 (5)	0.0254 (6)	0.0011 (4)	−0.0012 (4)	0.0002 (4)
S1	0.0183 (5)	0.0418 (6)	0.0253 (6)	0.0041 (4)	−0.0039 (4)	0.0001 (4)
O1	0.0097 (11)	0.0319 (13)	0.0286 (16)	0.0078 (10)	−0.0013 (10)	−0.0016 (10)
O2	0.0102 (11)	0.0251 (12)	0.0287 (15)	−0.0035 (9)	−0.0003 (10)	0.0007 (10)
O3	0.0090 (11)	0.0259 (12)	0.0311 (16)	−0.0025 (9)	−0.0037 (10)	−0.0022 (10)
N1	0.0093 (14)	0.0271 (16)	0.0282 (19)	−0.0002 (12)	−0.0046 (12)	0.0010 (13)
N2	0.0068 (13)	0.0291 (17)	0.0287 (19)	−0.0005 (12)	0.0022 (12)	0.0010 (13)
C1	0.0087 (16)	0.0267 (18)	0.030 (2)	0.0015 (14)	−0.0059 (15)	−0.0003 (15)
C2	0.0074 (16)	0.037 (2)	0.028 (2)	−0.0006 (15)	−0.0028 (15)	−0.0053 (16)
C3	0.0164 (18)	0.041 (2)	0.025 (2)	0.0003 (16)	0.0000 (16)	−0.0053 (16)
C4	0.0109 (17)	0.0274 (19)	0.035 (2)	−0.0008 (14)	−0.0083 (15)	−0.0062 (15)
C5	0.0088 (17)	0.037 (2)	0.037 (3)	−0.0005 (15)	0.0000 (16)	0.0045 (17)
C6	0.0208 (19)	0.037 (2)	0.031 (2)	0.0005 (16)	0.0033 (17)	0.0057 (17)
C7	0.0173 (19)	0.053 (3)	0.044 (3)	0.0011 (18)	−0.0110 (18)	−0.005 (2)
C8	0.0154 (17)	0.0243 (18)	0.025 (2)	−0.0019 (14)	−0.0005 (15)	−0.0022 (14)
C9	0.0120 (17)	0.0276 (19)	0.039 (3)	0.0033 (14)	−0.0042 (15)	−0.0014 (16)
C10	0.0104 (17)	0.035 (2)	0.045 (3)	0.0011 (15)	−0.0036 (16)	−0.0060 (18)
C11	0.0216 (19)	0.0244 (19)	0.042 (3)	−0.0039 (15)	0.0015 (17)	−0.0068 (17)
C12	0.028 (2)	0.0241 (19)	0.049 (3)	0.0052 (16)	−0.0078 (18)	0.0010 (17)
C13	0.0134 (17)	0.034 (2)	0.041 (3)	0.0020 (16)	−0.0046 (16)	0.0004 (17)
C14	0.033 (2)	0.032 (2)	0.071 (4)	−0.0046 (18)	0.002 (2)	−0.007 (2)
C15	0.0163 (18)	0.040 (2)	0.052 (3)	−0.0080 (17)	0.0056 (18)	−0.0021 (19)
C16	0.0117 (17)	0.039 (2)	0.046 (3)	−0.0004 (16)	0.0041 (16)	−0.0026 (18)
C17	0.0038 (15)	0.032 (2)	0.043 (3)	−0.0026 (14)	0.0005 (15)	−0.0032 (17)
C18	0.0139 (17)	0.037 (2)	0.038 (3)	−0.0031 (15)	0.0064 (16)	0.0042 (17)
C19	0.0194 (18)	0.035 (2)	0.030 (2)	0.0013 (16)	−0.0020 (16)	0.0037 (16)
C20	0.0071 (16)	0.038 (2)	0.036 (2)	0.0036 (15)	−0.0035 (15)	0.0000 (17)
C21	0.0051 (16)	0.037 (2)	0.043 (3)	−0.0018 (15)	−0.0024 (15)	−0.0024 (17)
C22	0.0195 (19)	0.051 (3)	0.045 (3)	0.0058 (18)	−0.0129 (17)	0.004 (2)

Ni1—N1	2.076 (3)	C9—H9	0.9500
Ni1—N1i	2.076 (3)	C10—C11	1.367 (4)
Ni1—N2	2.093 (2)	C10—H10	0.9500
Ni1—N2i	2.093 (2)	C11—C12	1.388 (4)
Ni1—O3i	2.106 (2)	C11—C14	1.504 (4)
Ni1—O3	2.106 (2)	C12—C13	1.385 (4)
P1—O3	1.491 (2)	C12—H12	0.9500
P1—O1	1.621 (2)	C13—H13	0.9500
P1—O2	1.627 (2)	C14—H14A	0.9800
P1—S1	1.9372 (14)	C14—H14B	0.9800
O1—C1	1.407 (4)	C14—H14C	0.9800
O2—C8	1.395 (3)	C15—C17	1.535 (4)
N1—C20	1.480 (4)	C15—H15A	0.9800
N1—C19	1.485 (4)	C15—H15C	0.9800
N1—H1	0.92 (3)	C15—H15B	0.9800
N2—C18	1.474 (4)	C16—C17	1.533 (4)
N2—C17	1.518 (4)	C16—H16A	0.9800
N2—H2	0.96 (3)	C16—H16C	0.9800
C1—C2	1.370 (4)	C16—H16B	0.9800
C1—C6	1.376 (4)	C17—C21i	1.529 (5)
C2—C3	1.384 (4)	C18—C19	1.522 (4)
C2—H2A	0.9500	C18—H18A	0.9900
C3—C4	1.399 (4)	C18—H18B	0.9900
C3—H3	0.9500	C19—H19B	0.9900
C4—C5	1.382 (5)	C19—H19A	0.9900
C4—C7	1.519 (4)	C20—C21	1.536 (4)
C5—C6	1.385 (4)	C20—C22	1.540 (4)
C5—H5	0.9500	C20—H20	1.0000
C6—H6	0.9500	C21—C17i	1.529 (5)
C7—H7A	0.9800	C21—H21B	0.9900
C7—H7C	0.9800	C21—H21A	0.9900
C7—H7B	0.9800	C22—H22C	0.9800
C8—C13	1.366 (4)	C22—H22B	0.9800
C8—C9	1.390 (4)	C22—H22A	0.9800
C9—C10	1.392 (4)
N1—Ni1—N1i	180.0	C11—C10—C9	122.2 (3)
N1—Ni1—N2	84.83 (11)	C11—C10—H10	118.9
N1i—Ni1—N2	95.17 (11)	C9—C10—H10	118.9
N1—Ni1—N2i	95.17 (11)	C10—C11—C12	118.1 (3)
N1i—Ni1—N2i	84.83 (11)	C10—C11—C14	121.4 (3)
N2—Ni1—N2i	180.0	C12—C11—C14	120.6 (3)
N1—Ni1—O3i	90.54 (10)	C13—C12—C11	120.8 (3)
N1i—Ni1—O3i	89.46 (10)	C13—C12—H12	119.6
N2—Ni1—O3i	93.63 (9)	C11—C12—H12	119.6
N2i—Ni1—O3i	86.37 (9)	C8—C13—C12	120.2 (3)
N1—Ni1—O3	89.46 (10)	C8—C13—H13	119.9
N1i—Ni1—O3	90.54 (10)	C12—C13—H13	119.9
N2—Ni1—O3	86.37 (9)	C11—C14—H14A	109.5
N2i—Ni1—O3	93.63 (9)	C11—C14—H14B	109.5
O3i—Ni1—O3	179.999 (1)	H14A—C14—H14B	109.5
O3—P1—O1	109.22 (12)	C11—C14—H14C	109.5
O3—P1—O2	102.67 (12)	H14A—C14—H14C	109.5
O1—P1—O2	103.25 (11)	H14B—C14—H14C	109.5
O3—P1—S1	120.90 (10)	C17—C15—H15A	109.5
O1—P1—S1	107.79 (10)	C17—C15—H15C	109.5
O2—P1—S1	111.61 (9)	H15A—C15—H15C	109.5
C1—O1—P1	122.1 (2)	C17—C15—H15B	109.5
C8—O2—P1	122.6 (2)	H15A—C15—H15B	109.5
P1—O3—Ni1	143.74 (12)	H15C—C15—H15B	109.5
C20—N1—C19	115.3 (2)	C17—C16—H16A	109.5
C20—N1—Ni1	115.0 (2)	C17—C16—H16C	109.5
C19—N1—Ni1	105.51 (19)	H16A—C16—H16C	109.5
C20—N1—H1	108.7 (19)	C17—C16—H16B	109.5
C19—N1—H1	106 (2)	H16A—C16—H16B	109.5
Ni1—N1—H1	105 (2)	H16C—C16—H16B	109.5
C18—N2—C17	115.9 (2)	N2—C17—C21i	108.1 (2)
C18—N2—Ni1	106.15 (18)	N2—C17—C16	110.2 (3)
C17—N2—Ni1	121.8 (2)	C21i—C17—C16	111.8 (3)
C18—N2—H2	110 (2)	N2—C17—C15	108.8 (3)
C17—N2—H2	107.0 (18)	C21i—C17—C15	108.2 (3)
Ni1—N2—H2	93.0 (17)	C16—C17—C15	109.7 (3)
C2—C1—C6	120.6 (3)	N2—C18—C19	107.6 (3)
C2—C1—O1	122.5 (3)	N2—C18—H18A	110.2
C6—C1—O1	116.8 (3)	C19—C18—H18A	110.2
C1—C2—C3	119.2 (3)	N2—C18—H18B	110.2
C1—C2—H2A	120.4	C19—C18—H18B	110.2
C3—C2—H2A	120.4	H18A—C18—H18B	108.5
C2—C3—C4	121.6 (3)	N1—C19—C18	109.0 (3)
C2—C3—H3	119.2	N1—C19—H19B	109.9
C4—C3—H3	119.2	C18—C19—H19B	109.9
C5—C4—C3	117.6 (3)	N1—C19—H19A	109.9
C5—C4—C7	120.2 (3)	C18—C19—H19A	109.9
C3—C4—C7	122.1 (3)	H19B—C19—H19A	108.3
C4—C5—C6	121.0 (3)	N1—C20—C21	108.9 (3)
C4—C5—H5	119.5	N1—C20—C22	112.0 (3)
C6—C5—H5	119.5	C21—C20—C22	110.3 (3)
C1—C6—C5	120.0 (3)	N1—C20—H20	108.5
C1—C6—H6	120.0	C21—C20—H20	108.5
C5—C6—H6	120.0	C22—C20—H20	108.5
C4—C7—H7A	109.5	C17i—C21—C20	120.1 (3)
C4—C7—H7C	109.5	C17i—C21—H21B	107.3
H7A—C7—H7C	109.5	C20—C21—H21B	107.3
C4—C7—H7B	109.5	C17i—C21—H21A	107.3
H7A—C7—H7B	109.5	C20—C21—H21A	107.3
H7C—C7—H7B	109.5	H21B—C21—H21A	106.9
C13—C8—C9	120.3 (3)	C20—C22—H22C	109.5
C13—C8—O2	121.1 (3)	C20—C22—H22B	109.5
C9—C8—O2	118.6 (3)	H22C—C22—H22B	109.5
C8—C9—C10	118.4 (3)	C20—C22—H22A	109.5
C8—C9—H9	120.8	H22C—C22—H22A	109.5
C10—C9—H9	120.8	H22B—C22—H22A	109.5
O3—P1—O1—C1	−32.3 (3)	C2—C3—C4—C7	177.2 (3)
O2—P1—O1—C1	76.4 (2)	C3—C4—C5—C6	0.8 (5)
S1—P1—O1—C1	−165.4 (2)	C7—C4—C5—C6	−176.9 (3)
O3—P1—O2—C8	−179.0 (2)	C2—C1—C6—C5	−0.4 (5)
O1—P1—O2—C8	67.5 (2)	O1—C1—C6—C5	176.8 (3)
S1—P1—O2—C8	−48.0 (2)	C4—C5—C6—C1	−0.3 (5)
O1—P1—O3—Ni1	−177.58 (19)	P1—O2—C8—C13	−91.2 (4)
O2—P1—O3—Ni1	73.3 (2)	P1—O2—C8—C9	91.8 (3)
S1—P1—O3—Ni1	−51.7 (2)	C13—C8—C9—C10	−1.4 (5)
N1—Ni1—O3—P1	−144.9 (2)	O2—C8—C9—C10	175.6 (3)
N1i—Ni1—O3—P1	35.1 (2)	C8—C9—C10—C11	1.2 (5)
N2—Ni1—O3—P1	−60.0 (2)	C9—C10—C11—C12	−0.3 (5)
N2i—Ni1—O3—P1	120.0 (2)	C9—C10—C11—C14	−179.8 (3)
N2—Ni1—N1—C20	−143.3 (2)	C10—C11—C12—C13	−0.6 (6)
N2i—Ni1—N1—C20	36.7 (2)	C14—C11—C12—C13	178.9 (3)
O3i—Ni1—N1—C20	123.1 (2)	C9—C8—C13—C12	0.6 (5)
O3—Ni1—N1—C20	−56.9 (2)	O2—C8—C13—C12	−176.3 (3)
N2—Ni1—N1—C19	−15.08 (19)	C11—C12—C13—C8	0.5 (5)
N2i—Ni1—N1—C19	164.92 (19)	C18—N2—C17—C21i	−173.6 (3)
O3i—Ni1—N1—C19	−108.67 (19)	Ni1—N2—C17—C21i	−41.9 (3)
O3—Ni1—N1—C19	71.33 (19)	C18—N2—C17—C16	−51.1 (4)
N1—Ni1—N2—C18	−15.2 (2)	Ni1—N2—C17—C16	80.6 (3)
N1i—Ni1—N2—C18	164.8 (2)	C18—N2—C17—C15	69.2 (4)
O3i—Ni1—N2—C18	75.0 (2)	Ni1—N2—C17—C15	−159.1 (2)
O3—Ni1—N2—C18	−105.0 (2)	C17—N2—C18—C19	−179.2 (3)
N1—Ni1—N2—C17	−150.8 (2)	Ni1—N2—C18—C19	42.2 (3)
N1i—Ni1—N2—C17	29.2 (2)	C20—N1—C19—C18	170.7 (3)
O3i—Ni1—N2—C17	−60.6 (2)	Ni1—N1—C19—C18	42.7 (3)
O3—Ni1—N2—C17	119.4 (2)	N2—C18—C19—N1	−58.6 (3)
P1—O1—C1—C2	−52.2 (4)	C19—N1—C20—C21	177.5 (3)
P1—O1—C1—C6	130.7 (3)	Ni1—N1—C20—C21	−59.3 (3)
C6—C1—C2—C3	0.7 (5)	C19—N1—C20—C22	55.2 (4)
O1—C1—C2—C3	−176.3 (3)	Ni1—N1—C20—C22	178.4 (2)
C1—C2—C3—C4	−0.3 (5)	N1—C20—C21—C17i	79.5 (4)
C2—C3—C4—C5	−0.4 (5)	C22—C20—C21—C17i	−157.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.92 (3)	2.66 (3)	3.574 (3)	171 (3)
N2—H2···O2	0.96 (3)	2.27 (3)	3.234 (3)	178 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.92 (3)	2.66 (3)	3.574 (3)	171 (3)
N2—H2⋯O2	0.96 (3)	2.27 (3)	3.234 (3)	178 (3)

Symmetry code: (i) .