[N,N′-Bis-(o-sulfido­benzyl­idene)-1,3-di­amino­propane]­nickel(II) 1,4-dioxane solvate

Taylor, M.K.; Reglinski, J.; Wallace, D.

doi:10.1107/S1600536804011882

metal-organic compounds

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ISSN: 2056-9890

Volume 60| Part 6| June 2004| Pages m850-m851

https://doi.org/10.1107/S1600536804011882

[N,N′-Bis-(o-sulfidobenzylidene)-1,3-diaminopropane]nickel(II) 1,4-dioxane solvate

Michelle K. Taylor,^a ^* John Reglinski ^a and Dawn Wallace ^a

^aDepartment of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral St., Glasgow G1 1XL, Scotland
^*Correspondence e-mail: michelle.k.taylor@strath.ac.uk

(Received 5 May 2004; accepted 17 May 2004; online 22 May 2004)

The title tetradentate Schiff base complex (systematic name: {2,2′-[propane-1,3-diylbis(nitrilomethylidyne)]benzenethiolato-κ⁴S,N,N′,S′}nickel(II) 1,4-dioxane solvate), [Ni(C₁₇H₁₆N₂S₂)]·C₄H₈O₂, contains an Ni atom coordinated within a tetrahedrally distorted planar N₂S₂ environment, with average Ni—N and Ni—S bond lengths of 1.922 (1) and 2.167 (1) Å, respectively.

Comment

As part of our ongoing studies (Reglinski et al., 2002a ,b ) on tetradentate Schiff base complexes with N₂X₂ donor sets and varying backbone lengths, the preparation of N₂S₂ complexes of this type was of interest. Eichorn & Goswami (1999 ) reported the use of a novel Schiff base semi-template for the formation of Ni^II complexes with mixed N/S-donating chelates. This method involves the reaction in ethanol of Ni^II complexes containing primary amine chelates and 2,2′-dithiodibenzaldehyde (DTDB). In order to assess the applicability of extending this method to the preparation of complexes with longer backbones, the title compound, (I), was prepared by this method. Crystals were obtained and the unit cell was found to be different from that of the previously reported structure of this compound (Gomes et al., 1999 ), which has two independent nickel complex molecules in the asymmetric unit.

Figure 1
View of (I

) (50% probability displacement ellipsoids). The solvent molecule has been omitted.

Experimental

The reaction of tris(propylenediamine)nickel(II)chloride and DTDB (Kasmai & Mischke, 1989 ) in ethanol produced a brown solid. Analysis found: C 54.28, H 4.58, N 7.04, S 16.62%; calculated for C₁₇H₁₆N₂NiS₂: C 55.01, H 4.34, N 7.55, S 17.28%; ¹H NMR (270 MHz; solvent CDCl₃): δ 7.83 (s, 2H, CH=N), 7.69 (d, 2H, aromatic), 7.22 (d, 2H, aromatic), 7.15 (t, 2H, aromatic), 7.00 (t, 2H, aromatic), 3.99 (t, 4H, =NCH₂—), 2.09 (p, 2H, CCH₂C). Dark-brown crystals suitable for X-ray analysis were obtained by slow evaporation of a dioxane solution of the brown solid.

Crystal data

[Ni(C₁₇H₁₆N₂S₂)]·C₄H₈O₂
M_r = 459.25
Triclinic, $[P\overline 1]$
a = 9.2099 (3) Å
b = 9.3828 (2) Å
c = 13.2522 (4) Å
α = 77.392 (2)°
β = 88.719 (2)°
γ = 66.761 (2)°
V = 1024.30 (5) Å³
Z = 2
D_x = 1.489 Mg m⁻³
Mo Kα radiation
Cell parameters from 4660 reflections
θ = 1.6–27.5°
μ = 1.17 mm⁻¹
T = 123 (2) K
Prism, brown
0.25 × 0.25 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: none
9186 measured reflections
4660 independent reflections
3758 reflections with I > 2σ(I)
R_int = 0.029
θ_max = 27.5°
h = −11 → 11
k = −11 → 12
l = −17 → 17

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.057
S = 1.03
4660 reflections
349 parameters
All H-atom parameters refined
w = 1/[σ²(F_o²) + (0.0146P)² + 0.5180P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.033
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N1—Ni1	1.9140 (14)
N2—Ni1	1.9307 (15)
S1—Ni1	2.1760 (5)
S2—Ni1	2.1574 (5)

N1—Ni1—S2	170.86 (4)
N2—Ni1—S1	169.35 (4)

All H atoms were found in a difference Fourier map and were refined isotropically [C—H = 0.90 (2)–1.02 (2) Å].

Data collection: DENZO (Otwinowski & Minor, 1997 ) and COLLECT (Hooft, 1998 ); cell refinement: DENZO; data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536804011882/ac6101sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536804011882/ac6101Isup2.hkl

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT'; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top

Crystal data top

[Ni(C₁₇H₁₆N₂S₂)]·C₄H₈O₂	Z = 2
M_r = 459.25	F(000) = 480
Triclinic, P1	D_x = 1.489 Mg m⁻³
a = 9.2099 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3828 (2) Å	Cell parameters from 4660 reflections
c = 13.2522 (4) Å	θ = 1.6–27.5°
α = 77.392 (2)°	µ = 1.17 mm⁻¹
β = 88.719 (2)°	T = 123 K
γ = 66.761 (2)°	Prism, brown
V = 1024.30 (5) Å³	0.25 × 0.25 × 0.2 mm

Data collection top

Nonius KappaCCD diffractometer	R_int = 0.029
φ and ω scans	θ_max = 27.5°, θ_min = 1.6°
9186 measured reflections	h = −11→11
4660 independent reflections	k = −11→12
3758 reflections with I > 2σ(I)	l = −17→17

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.029	w = 1/[σ²(F_o²) + (0.0146P)² + 0.518P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.057	(Δ/σ)_max = 0.033
S = 1.03	Δρ_max = 0.36 e Å⁻³
4660 reflections	Δρ_min = −0.29 e Å⁻³
349 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2710 (2)	0.7389 (2)	0.57855 (14)	0.0159 (4)
C2	0.1408 (2)	0.7676 (2)	0.63999 (15)	0.0189 (4)
C3	0.1601 (2)	0.7008 (2)	0.74544 (15)	0.0216 (4)
C4	0.3099 (2)	0.6008 (2)	0.79286 (16)	0.0235 (4)
C5	0.4386 (2)	0.5709 (2)	0.73374 (15)	0.0209 (4)
C6	0.4231 (2)	0.6404 (2)	0.62742 (14)	0.0163 (4)
C7	0.5667 (2)	0.5992 (2)	0.57264 (14)	0.0173 (4)
C8	0.7439 (2)	0.6049 (2)	0.44351 (15)	0.0169 (4)
C9	0.8365 (2)	0.7036 (2)	0.45712 (16)	0.0193 (4)
C10	0.7314 (2)	0.8817 (2)	0.43429 (15)	0.0192 (4)
C11	0.6252 (2)	1.0193 (2)	0.26429 (14)	0.0165 (4)
C12	0.5229 (2)	1.0864 (2)	0.16979 (14)	0.0178 (4)
C13	0.5847 (2)	1.1463 (2)	0.08023 (16)	0.0224 (4)
C14	0.4958 (2)	1.2121 (2)	−0.01327 (16)	0.0257 (5)
C15	0.3415 (2)	1.2220 (2)	−0.01875 (15)	0.0240 (4)
C16	0.2771 (2)	1.1676 (2)	0.06836 (15)	0.0213 (4)
C17	0.3659 (2)	1.0981 (2)	0.16450 (14)	0.0168 (4)
N1	0.58507 (17)	0.67295 (17)	0.48251 (11)	0.0147 (3)
N2	0.61009 (17)	0.92791 (17)	0.34786 (11)	0.0156 (3)
S1	0.23398 (5)	0.81892 (5)	0.44491 (3)	0.01690 (10)
S2	0.26934 (5)	1.04149 (6)	0.27094 (4)	0.02131 (11)
Ni1	0.44140 (3)	0.85851 (3)	0.387643 (18)	0.01469 (7)
O1	0.87627 (16)	0.38996 (16)	0.74835 (10)	0.0273 (3)
O2	0.91928 (17)	0.23564 (16)	0.96165 (10)	0.0287 (3)
C19	0.9658 (2)	0.2222 (2)	0.78346 (16)	0.0240 (4)
C20	0.9075 (3)	0.1581 (3)	0.88208 (16)	0.0267 (5)
C21	0.8345 (3)	0.4039 (3)	0.92787 (17)	0.0309 (5)
C22	0.8898 (3)	0.4680 (3)	0.82688 (18)	0.0325 (5)
H2	0.041 (2)	0.834 (2)	0.6093 (14)	0.020 (5)*
H3	0.071 (2)	0.725 (2)	0.7839 (15)	0.020 (5)*
H4	0.323 (2)	0.553 (2)	0.8650 (16)	0.028 (6)*
H5	0.544 (2)	0.504 (2)	0.7636 (15)	0.029 (6)*
H7	0.657 (2)	0.506 (2)	0.6091 (13)	0.013 (5)*
H8A	0.799 (2)	0.495 (2)	0.4793 (13)	0.012 (5)*
H8B	0.729 (2)	0.607 (2)	0.3686 (15)	0.021 (5)*
H9A	0.879 (2)	0.674 (2)	0.5288 (15)	0.017 (5)*
H9B	0.919 (2)	0.684 (2)	0.4129 (14)	0.016 (5)*
H10A	0.676 (2)	0.909 (2)	0.4961 (15)	0.016 (5)*
H10B	0.794 (2)	0.944 (2)	0.4160 (14)	0.014 (5)*
H11	0.721 (2)	1.047 (2)	0.2618 (13)	0.015 (5)*
H13	0.688 (2)	1.140 (2)	0.0862 (16)	0.030 (6)*
H14	0.537 (2)	1.248 (2)	−0.0743 (15)	0.022 (5)*
H15	0.281 (2)	1.264 (2)	−0.0846 (15)	0.018 (5)*
H16	0.172 (2)	1.173 (2)	0.0642 (14)	0.019 (5)*
H19A	0.955 (2)	0.172 (2)	0.7274 (15)	0.024 (5)*
H19B	1.079 (2)	0.202 (2)	0.7942 (14)	0.020 (5)*
H20A	0.795 (2)	0.172 (2)	0.8714 (15)	0.027 (6)*
H20B	0.976 (2)	0.040 (2)	0.9083 (15)	0.028 (5)*
H21A	0.853 (2)	0.455 (2)	0.9808 (16)	0.027 (6)*
H21B	0.716 (3)	0.432 (3)	0.9209 (16)	0.036 (6)*
H22A	0.999 (3)	0.455 (2)	0.8372 (15)	0.027 (6)*
H22B	0.824 (2)	0.583 (3)	0.7993 (16)	0.033 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0180 (9)	0.0101 (8)	0.0197 (9)	−0.0052 (7)	0.0012 (7)	−0.0044 (7)
C2	0.0155 (9)	0.0148 (9)	0.0263 (11)	−0.0061 (8)	0.0007 (8)	−0.0046 (8)
C3	0.0217 (10)	0.0197 (10)	0.0237 (10)	−0.0085 (8)	0.0080 (9)	−0.0056 (8)
C4	0.0266 (11)	0.0213 (10)	0.0192 (10)	−0.0085 (9)	0.0033 (9)	−0.0003 (8)
C5	0.0191 (10)	0.0196 (10)	0.0211 (10)	−0.0071 (8)	−0.0028 (8)	0.0003 (8)
C6	0.0170 (9)	0.0126 (9)	0.0185 (9)	−0.0057 (7)	0.0010 (8)	−0.0026 (7)
C7	0.0165 (9)	0.0132 (9)	0.0215 (10)	−0.0051 (8)	−0.0020 (8)	−0.0036 (8)
C8	0.0140 (9)	0.0127 (9)	0.0211 (10)	−0.0025 (7)	0.0018 (8)	−0.0034 (8)
C9	0.0152 (9)	0.0204 (10)	0.0215 (10)	−0.0074 (8)	0.0012 (8)	−0.0023 (8)
C10	0.0197 (10)	0.0187 (10)	0.0213 (10)	−0.0095 (8)	−0.0021 (8)	−0.0052 (8)
C11	0.0143 (9)	0.0129 (9)	0.0227 (10)	−0.0050 (7)	0.0033 (8)	−0.0060 (8)
C12	0.0209 (10)	0.0124 (9)	0.0191 (10)	−0.0059 (7)	0.0017 (8)	−0.0032 (7)
C13	0.0194 (10)	0.0180 (10)	0.0276 (11)	−0.0060 (8)	0.0048 (9)	−0.0037 (8)
C14	0.0300 (11)	0.0215 (11)	0.0201 (11)	−0.0077 (9)	0.0050 (9)	0.0011 (8)
C15	0.0310 (11)	0.0189 (10)	0.0188 (10)	−0.0079 (9)	−0.0034 (9)	−0.0010 (8)
C16	0.0205 (10)	0.0176 (10)	0.0239 (10)	−0.0069 (8)	−0.0033 (8)	−0.0019 (8)
C17	0.0187 (9)	0.0117 (9)	0.0190 (9)	−0.0049 (7)	0.0016 (8)	−0.0037 (7)
N1	0.0134 (7)	0.0115 (7)	0.0190 (8)	−0.0042 (6)	0.0017 (6)	−0.0044 (6)
N2	0.0159 (8)	0.0118 (7)	0.0189 (8)	−0.0049 (6)	−0.0010 (6)	−0.0045 (6)
S1	0.0150 (2)	0.0171 (2)	0.0173 (2)	−0.00633 (18)	−0.00101 (18)	−0.00146 (18)
S2	0.0148 (2)	0.0223 (3)	0.0207 (2)	−0.00485 (19)	0.00009 (19)	0.0028 (2)
Ni1	0.01358 (12)	0.01291 (12)	0.01610 (12)	−0.00437 (9)	0.00019 (9)	−0.00203 (9)
O1	0.0315 (8)	0.0223 (7)	0.0221 (7)	−0.0061 (6)	−0.0015 (6)	−0.0019 (6)
O2	0.0351 (8)	0.0277 (8)	0.0203 (7)	−0.0094 (7)	−0.0020 (6)	−0.0048 (6)
C19	0.0222 (11)	0.0226 (11)	0.0251 (11)	−0.0063 (9)	−0.0007 (9)	−0.0060 (9)
C20	0.0319 (12)	0.0236 (11)	0.0254 (11)	−0.0120 (10)	0.0002 (9)	−0.0053 (9)
C21	0.0341 (13)	0.0282 (12)	0.0280 (12)	−0.0072 (10)	0.0000 (10)	−0.0117 (10)
C22	0.0353 (13)	0.0208 (12)	0.0379 (13)	−0.0082 (10)	−0.0017 (11)	−0.0049 (10)

Geometric parameters (Å, º) top

C1—C2	1.404 (3)	C12—C17	1.408 (3)
C1—C6	1.412 (2)	C13—C14	1.378 (3)
C1—S1	1.7495 (18)	C13—H13	0.94 (2)
C2—C3	1.385 (3)	C14—C15	1.390 (3)
C2—H2	0.921 (19)	C14—H14	0.94 (2)
C3—C4	1.392 (3)	C15—C16	1.377 (3)
C3—H3	0.933 (19)	C15—H15	0.963 (18)
C4—C5	1.375 (3)	C16—C17	1.407 (3)
C4—H4	0.95 (2)	C16—H16	0.948 (19)
C5—C6	1.402 (3)	C17—S2	1.7471 (19)
C5—H5	0.96 (2)	N1—Ni1	1.9140 (14)
C6—C7	1.450 (3)	N2—Ni1	1.9307 (15)
C7—N1	1.287 (2)	S1—Ni1	2.1760 (5)
C7—H7	0.973 (18)	S2—Ni1	2.1574 (5)
C8—N1	1.479 (2)	O1—C22	1.430 (2)
C8—C9	1.523 (3)	O1—C19	1.431 (2)
C8—H8A	0.968 (18)	O2—C21	1.427 (2)
C8—H8B	0.999 (19)	O2—C20	1.434 (2)
C9—C10	1.529 (3)	C19—C20	1.496 (3)
C9—H9A	0.975 (18)	C19—H19A	0.990 (19)
C9—H9B	0.937 (19)	C19—H19B	0.990 (19)
C10—N2	1.485 (2)	C20—H20A	1.00 (2)
C10—H10A	0.984 (19)	C20—H20B	1.02 (2)
C10—H10B	0.965 (19)	C21—C22	1.507 (3)
C11—N2	1.286 (2)	C21—H21A	0.98 (2)
C11—C12	1.447 (2)	C21—H21B	1.02 (2)
C11—H11	1.009 (19)	C22—H22A	0.97 (2)
C12—C13	1.407 (3)	C22—H22B	0.99 (2)

C2—C1—C6	118.10 (17)	C15—C14—H14	118.7 (12)
C2—C1—S1	117.96 (13)	C16—C15—C14	120.51 (19)
C6—C1—S1	123.85 (14)	C16—C15—H15	120.1 (12)
C3—C2—C1	121.20 (17)	C14—C15—H15	119.4 (11)
C3—C2—H2	119.9 (12)	C15—C16—C17	121.23 (19)
C1—C2—H2	118.9 (12)	C15—C16—H16	120.4 (12)
C2—C3—C4	120.49 (19)	C17—C16—H16	118.4 (12)
C2—C3—H3	118.6 (12)	C16—C17—C12	118.25 (17)
C4—C3—H3	120.9 (12)	C16—C17—S2	117.24 (14)
C5—C4—C3	119.05 (19)	C12—C17—S2	124.42 (14)
C5—C4—H4	120.2 (12)	C7—N1—C8	115.75 (15)
C3—C4—H4	120.7 (12)	C7—N1—Ni1	131.25 (13)
C4—C5—C6	121.69 (18)	C8—N1—Ni1	113.00 (11)
C4—C5—H5	121.6 (12)	C11—N2—C10	115.91 (16)
C6—C5—H5	116.7 (13)	C11—N2—Ni1	130.86 (12)
C5—C6—C1	119.42 (17)	C10—N2—Ni1	112.78 (12)
C5—C6—C7	116.91 (16)	C1—S1—Ni1	107.57 (6)
C1—C6—C7	123.59 (16)	C17—S2—Ni1	109.63 (6)
N1—C7—C6	126.55 (17)	N1—Ni1—N2	90.94 (6)
N1—C7—H7	118.3 (11)	N1—Ni1—S2	170.86 (4)
C6—C7—H7	115.2 (11)	N2—Ni1—S2	94.62 (5)
N1—C8—C9	109.44 (15)	N1—Ni1—S1	93.17 (5)
N1—C8—H8A	110.1 (11)	N2—Ni1—S1	169.35 (4)
C9—C8—H8A	111.4 (10)	S2—Ni1—S1	82.624 (19)
N1—C8—H8B	107.8 (11)	C22—O1—C19	109.04 (15)
C9—C8—H8B	110.6 (11)	C21—O2—C20	110.24 (15)
H8A—C8—H8B	107.4 (14)	O1—C19—C20	110.75 (16)
C8—C9—C10	111.96 (15)	O1—C19—H19A	107.1 (11)
C8—C9—H9A	109.7 (11)	C20—C19—H19A	111.4 (12)
C10—C9—H9A	106.7 (11)	O1—C19—H19B	108.9 (11)
C8—C9—H9B	109.0 (11)	C20—C19—H19B	110.2 (11)
C10—C9—H9B	109.8 (11)	H19A—C19—H19B	108.4 (15)
H9A—C9—H9B	109.7 (15)	O2—C20—C19	110.81 (17)
N2—C10—C9	111.59 (15)	O2—C20—H20A	109.5 (11)
N2—C10—H10A	107.9 (10)	C19—C20—H20A	111.1 (12)
C9—C10—H10A	109.6 (11)	O2—C20—H20B	106.8 (11)
N2—C10—H10B	108.2 (10)	C19—C20—H20B	109.9 (12)
C9—C10—H10B	110.9 (11)	H20A—C20—H20B	108.6 (16)
H10A—C10—H10B	108.4 (15)	O2—C21—C22	111.31 (18)
N2—C11—C12	127.90 (17)	O2—C21—H21A	108.6 (12)
N2—C11—H11	117.6 (10)	C22—C21—H21A	108.6 (12)
C12—C11—H11	114.4 (10)	O2—C21—H21B	110.3 (12)
C13—C12—C17	119.45 (17)	C22—C21—H21B	110.5 (12)
C13—C12—C11	117.09 (17)	H21A—C21—H21B	107.4 (16)
C17—C12—C11	123.43 (17)	O1—C22—C21	111.26 (18)
C14—C13—C12	121.09 (19)	O1—C22—H22A	110.3 (12)
C14—C13—H13	121.1 (13)	C21—C22—H22A	109.7 (12)
C12—C13—H13	117.9 (13)	O1—C22—H22B	105.5 (12)
C13—C14—C15	119.4 (2)	C21—C22—H22B	111.7 (13)
C13—C14—H14	121.8 (12)	H22A—C22—H22B	108.3 (17)

C6—C1—C2—C3	−0.3 (3)	C9—C8—N1—Ni1	78.07 (16)
S1—C1—C2—C3	176.39 (14)	C12—C11—N2—C10	−177.98 (17)
C1—C2—C3—C4	−1.2 (3)	C12—C11—N2—Ni1	−6.4 (3)
C2—C3—C4—C5	0.8 (3)	C9—C10—N2—C11	−113.05 (19)
C3—C4—C5—C6	1.0 (3)	C9—C10—N2—Ni1	73.81 (18)
C4—C5—C6—C1	−2.5 (3)	C2—C1—S1—Ni1	152.10 (12)
C4—C5—C6—C7	−179.45 (17)	C6—C1—S1—Ni1	−31.40 (16)
C2—C1—C6—C5	2.1 (3)	C16—C17—S2—Ni1	156.60 (12)
S1—C1—C6—C5	−174.40 (14)	C12—C17—S2—Ni1	−26.83 (17)
C2—C1—C6—C7	178.84 (16)	C7—N1—Ni1—N2	142.94 (16)
S1—C1—C6—C7	2.3 (2)	C8—N1—Ni1—N2	−37.06 (12)
C5—C6—C7—N1	−164.25 (17)	C7—N1—Ni1—S1	−27.23 (16)
C1—C6—C7—N1	18.9 (3)	C8—N1—Ni1—S1	152.77 (11)
N1—C8—C9—C10	−38.6 (2)	C11—N2—Ni1—N1	155.57 (16)
C8—C9—C10—N2	−36.3 (2)	C10—N2—Ni1—N1	−32.60 (12)
N2—C11—C12—C13	−163.22 (18)	C11—N2—Ni1—S2	−17.17 (16)
N2—C11—C12—C17	18.7 (3)	C10—N2—Ni1—S2	154.66 (11)
C17—C12—C13—C14	−1.9 (3)	C11—N2—Ni1—S1	−91.7 (3)
C11—C12—C13—C14	179.87 (17)	C10—N2—Ni1—S1	80.1 (3)
C12—C13—C14—C15	1.2 (3)	C17—S2—Ni1—N2	28.01 (8)
C13—C14—C15—C16	0.4 (3)	C17—S2—Ni1—S1	−162.34 (6)
C14—C15—C16—C17	−1.2 (3)	C1—S1—Ni1—N1	35.44 (7)
C15—C16—C17—C12	0.5 (3)	C1—S1—Ni1—N2	−77.1 (3)
C15—C16—C17—S2	177.25 (15)	C1—S1—Ni1—S2	−152.71 (6)
C13—C12—C17—C16	1.1 (3)	C22—O1—C19—C20	58.8 (2)
C11—C12—C17—C16	179.17 (17)	C21—O2—C20—C19	56.4 (2)
C13—C12—C17—S2	−175.45 (14)	O1—C19—C20—O2	−59.1 (2)
C11—C12—C17—S2	2.6 (3)	C20—O2—C21—C22	−55.0 (2)
C6—C7—N1—C8	−179.34 (16)	C19—O1—C22—C21	−57.4 (2)
C6—C7—N1—Ni1	0.7 (3)	O2—C21—C22—O1	56.4 (2)
C9—C8—N1—C7	−101.93 (18)

Acknowledgements

JR wishes to thank the Cunningham Trust (Scotland) for financial assistance.

References

Eichorn, D. M. & Goswami, N. (1999). Inorg. Chem. 38, 4329–4333. Web of Science CSD CrossRef Google Scholar
Gomes, L., Pereira, E. & De Castro, B. (1999). Acta Cryst. C55, 1061–1063. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kasmai, H. S. & Mischke, S. G. (1989). Synthesis, pp. 763–765. CrossRef Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr and R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Reglinski, J., Morris, S. & Stevenson, D. E. (2002a). Polyhedron, 21, 2167–2174. Web of Science CSD CrossRef CAS Google Scholar
Reglinski, J., Morris, S. & Stevenson, D. E. (2002b). Polyhedron, 21, 2175–2182. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar

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