Bis(2,2'-bipyridyl-κ(2) N,N')(sulfato-κ(2) O,O')nickel(II) 2.5-hydrate.

The title compound, [Ni(SO4)(C10H8N2)2]·2.5H2O, is a nickel(II) complex with a distorted octa-hedral coordination geometry. The Ni(II) atom is bonded by two O atoms of the bidentate chelating sulfate ligand and the four N atoms of two chelating 2,2'-bi-pyridine ligands. The Ni-N bond lengths range from 2.059 (3) to 2.075 (3) Å and the Ni-O bond lengths are 2.098 (3) and 2.123 (3) Å. The bipyridyl ligands are both close to planar (r.m.s. deviations of 0.254 and 0.0572 Å) and are almost orthogonal, making a dihedral angle of 82.77 (1)°. In the crystal, the complex and water mol-ecules are connected by O-H⋯O hydrogen bonds. Inter-estingly, six water mol-ecules form a chain linking two complex mol-ecules via sulfate O atoms. There are also stacking inter-actions between the aromatic rings of neighbouring 2,2'-bi-pyridine ligands with shortest non-covalent contacts of 3.268 (6), 3.393 (6) and 3.435 (5) Å. One of the three unique water molecules shows half-occupation.

Related literature

For applications of the 2,2′-bipyridyl ligand, see: Fritsky et al. (2004 ▶, 2006 ▶); Kanderal et al. (2005 ▶). For related structures, see: Fritsky et al. (1998 ▶, 2000 ▶); Moroz et al. (2010 ▶, 2012 ▶); Sliva et al. (1997 ▶); Świątek-Kozłowska et al. (2000 ▶); Iskenderov et al. (2009 ▶).

Experimental

Crystal data

[Ni(SO4)(C10H8N2)2]·2.5n class="Chemical">H2O

M = 512.18

Triclinic,

a = 10.045 (2) Å

b = 10.393 (2) Å

c = 11.028 (2) Å

α = 99.42 (3)°

β = 101.97 (3)°

γ = 98.56 (3)°

V = 1091.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.03 mm−1

T = 293 K

0.32 × 0.22 × 0.11 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: multi-scan (North et al., 1968 ▶) T min = 0.765, T max = 0.897

3228 measured reflections

3021 independent reflections

2527 reflections with I > 2σ(I)

R int = 0.030

3 standard reflections every 100 reflections intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.124

S = 1.07

3021 reflections

301 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.76 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014219/sj5321sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014219/sj5321Isup2.hkl

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

[Ni(SO4)(C10H8N2)2]·2.5H2O	Z = 2
Mr = 512.18	F(000) = 530
Triclinic, P1	Dx = 1.559 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.045 (2) Å	Cell parameters from 1565 reflections
b = 10.393 (2) Å	θ = 3.0–25.5°
c = 11.028 (2) Å	µ = 1.03 mm−1
α = 99.42 (3)°	T = 293 K
β = 101.97 (3)°	Block, blue
γ = 98.56 (3)°	0.32 × 0.22 × 0.11 mm
V = 1091.0 (4) Å3

Enraf–Nonius CAD-4 diffractometer	3021 independent reflections
Radiation source: fine-focus sealed tube	2527 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.030
Detector resolution: 9 pixels mm-1	θmax = 26.1°, θmin = 1.9°
profile data from ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.765, Tmax = 0.897	l = −12→12
3228 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0784P)2 + 0.7731P] where P = (Fo2 + 2Fc2)/3
3021 reflections	(Δ/σ)max < 0.001
301 parameters	Δρmax = 0.76 e Å−3
12 restraints	Δρmin = −0.44 e Å−3

Experimental. The H2O H atoms of the solvate water molecules were located from the difference Fourier map but constrained to ride on their parent atom, with Uiso = 1.5 Ueq(parent atom). One of the solvate water molecule was included into refinement with the occupancy factor of 0.5 (as an attempt to refine it with free variation of the occupancy factor resulted in its value of 1/2, and as O3W forms an H-bond with the tranlsational O3W water molecule through the hydrogen atom H1W3 which limits the occupancy of the latter by 1/2). The C—H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 and Uiso = 1.2Ueq(parent atom).

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	Occ. (<1)
S1	0.05920 (10)	0.23826 (10)	0.38907 (9)	0.0340 (3)
Ni1	0.23116 (5)	0.29554 (5)	0.24003 (4)	0.0288 (2)
O1	0.2111 (3)	0.2317 (3)	0.4097 (2)	0.0345 (6)
O2	0.0295 (3)	0.2855 (3)	0.2672 (2)	0.0342 (6)
O3	0.0352 (3)	0.3311 (3)	0.4914 (3)	0.0478 (8)
O4	−0.0214 (3)	0.1049 (3)	0.3732 (3)	0.0548 (9)
O1W	0.7471 (4)	−0.0268 (4)	0.4408 (4)	0.0751 (11)
H1W1	0.7839	−0.0894	0.4895	0.113*
H2W1	0.8304	0.0141	0.4490	0.113*
O2W	0.5607 (10)	−0.0896 (10)	0.2062 (10)	0.225 (4)
H1W2	0.5395	−0.1799	0.1620	0.337*
H2W2	0.6204	−0.0800	0.2757	0.337*
O3W	0.482 (2)	0.631 (2)	0.0491 (18)	0.237 (9)	0.50
H1W3	0.5088	0.5500	0.0081	0.356*	0.50
H2W3	0.4120	0.6030	0.0716	0.356*	0.50
N1	0.1856 (3)	0.3201 (3)	0.0539 (3)	0.0354 (8)
N2	0.2016 (3)	0.1024 (3)	0.1437 (3)	0.0324 (7)
N3	0.2837 (3)	0.4950 (3)	0.3228 (3)	0.0300 (7)
N4	0.4444 (3)	0.3267 (3)	0.2655 (3)	0.0312 (7)
C1	0.1708 (5)	0.4330 (4)	0.0137 (4)	0.0459 (11)
H1	0.1829	0.5105	0.0737	0.055*
C2	0.1387 (6)	0.4396 (5)	−0.1111 (4)	0.0542 (13)
H2	0.1279	0.5198	−0.1353	0.065*
C3	0.1227 (5)	0.3263 (5)	−0.2006 (4)	0.0475 (11)
H3	0.1034	0.3288	−0.2862	0.057*
C4	0.1356 (5)	0.2089 (4)	−0.1611 (4)	0.0410 (10)
H4	0.1237	0.1306	−0.2201	0.049*
C5	0.1663 (4)	0.2082 (4)	−0.0339 (4)	0.0324 (9)
C6	0.1766 (4)	0.0860 (4)	0.0172 (4)	0.0313 (9)
C7	0.1606 (5)	−0.0371 (4)	−0.0592 (4)	0.0418 (10)
H7	0.1424	−0.0468	−0.1467	0.050*
C8	0.1722 (5)	−0.1456 (4)	−0.0033 (4)	0.0495 (12)
H8	0.1614	−0.2296	−0.0530	0.059*
C9	0.1998 (5)	−0.1289 (4)	0.1260 (4)	0.0465 (11)
H9	0.2099	−0.2007	0.1653	0.056*
C10	0.2123 (5)	−0.0038 (4)	0.1963 (4)	0.0416 (10)
H10	0.2288	0.0074	0.2838	0.050*
C11	0.1965 (4)	0.5742 (4)	0.3500 (4)	0.0359 (9)
H11	0.1029	0.5374	0.3345	0.043*
C12	0.2385 (4)	0.7071 (4)	0.3996 (4)	0.0401 (10)
H12	0.1745	0.7595	0.4164	0.048*
C13	0.3771 (5)	0.7620 (4)	0.4242 (4)	0.0471 (11)
H13	0.4081	0.8525	0.4566	0.057*
C14	0.4694 (5)	0.6806 (4)	0.3999 (4)	0.0447 (11)
H14	0.5638	0.7152	0.4174	0.054*
C15	0.4197 (4)	0.5473 (4)	0.3494 (3)	0.0327 (9)
C16	0.5110 (4)	0.4517 (4)	0.3221 (3)	0.0327 (9)
C17	0.6536 (4)	0.4860 (4)	0.3560 (4)	0.0398 (10)
H17	0.6972	0.5725	0.3954	0.048*
C18	0.7305 (5)	0.3903 (5)	0.3306 (4)	0.0470 (11)
H18	0.8268	0.4114	0.3538	0.056*
C19	0.6657 (5)	0.2657 (5)	0.2719 (4)	0.0494 (12)
H19	0.7163	0.2004	0.2526	0.059*
C20	0.5228 (4)	0.2372 (4)	0.2410 (4)	0.0421 (10)
H20	0.4787	0.1510	0.2010	0.051*

	U11	U22	U33	U12	U13	U23
S1	0.0296 (6)	0.0366 (6)	0.0294 (5)	−0.0008 (4)	0.0026 (4)	0.0003 (4)
Ni1	0.0278 (3)	0.0261 (3)	0.0256 (3)	−0.0002 (2)	0.0010 (2)	−0.0033 (2)
O1	0.0318 (15)	0.0384 (15)	0.0293 (14)	0.0058 (12)	0.0018 (12)	0.0038 (12)
O2	0.0278 (14)	0.0357 (15)	0.0313 (15)	0.0009 (12)	−0.0034 (12)	0.0026 (12)
O3	0.0407 (17)	0.063 (2)	0.0349 (16)	0.0123 (15)	0.0082 (13)	−0.0041 (14)
O4	0.053 (2)	0.0452 (18)	0.056 (2)	−0.0144 (15)	0.0058 (16)	0.0120 (16)
O1W	0.065 (2)	0.064 (2)	0.103 (3)	0.0146 (19)	0.017 (2)	0.036 (2)
O2W	0.204 (7)	0.213 (7)	0.244 (8)	0.038 (6)	0.016 (6)	0.058 (6)
O3W	0.237 (12)	0.248 (12)	0.222 (12)	0.012 (9)	0.059 (9)	0.057 (9)
N1	0.0380 (19)	0.0312 (18)	0.0312 (18)	0.0005 (15)	0.0042 (15)	0.0007 (15)
N2	0.0331 (18)	0.0304 (17)	0.0281 (18)	0.0024 (14)	0.0015 (14)	0.0006 (14)
N3	0.0271 (18)	0.0314 (17)	0.0264 (17)	0.0023 (14)	0.0018 (14)	0.0000 (13)
N4	0.0309 (17)	0.0341 (18)	0.0252 (16)	0.0058 (15)	0.0036 (14)	0.0012 (14)
C1	0.061 (3)	0.036 (2)	0.037 (2)	0.006 (2)	0.005 (2)	0.0060 (19)
C2	0.078 (4)	0.039 (3)	0.045 (3)	0.011 (2)	0.011 (3)	0.012 (2)
C3	0.054 (3)	0.056 (3)	0.031 (2)	0.007 (2)	0.007 (2)	0.012 (2)
C4	0.047 (3)	0.040 (2)	0.029 (2)	0.004 (2)	0.0042 (19)	−0.0028 (18)
C5	0.030 (2)	0.033 (2)	0.029 (2)	0.0028 (17)	0.0041 (17)	−0.0027 (17)
C6	0.026 (2)	0.033 (2)	0.030 (2)	0.0015 (17)	0.0029 (16)	−0.0012 (17)
C7	0.047 (3)	0.039 (2)	0.031 (2)	0.006 (2)	0.0030 (19)	−0.0060 (18)
C8	0.060 (3)	0.029 (2)	0.049 (3)	0.002 (2)	0.005 (2)	−0.005 (2)
C9	0.057 (3)	0.031 (2)	0.047 (3)	0.005 (2)	0.006 (2)	0.003 (2)
C10	0.046 (3)	0.039 (2)	0.035 (2)	0.004 (2)	0.0043 (19)	0.0034 (19)
C11	0.031 (2)	0.036 (2)	0.037 (2)	0.0028 (18)	0.0057 (18)	0.0021 (18)
C12	0.045 (3)	0.032 (2)	0.041 (2)	0.012 (2)	0.009 (2)	0.0012 (18)
C13	0.054 (3)	0.031 (2)	0.046 (3)	0.000 (2)	0.003 (2)	−0.0045 (19)
C14	0.037 (2)	0.036 (2)	0.046 (3)	−0.009 (2)	−0.001 (2)	−0.004 (2)
C15	0.034 (2)	0.035 (2)	0.025 (2)	0.0027 (18)	0.0016 (17)	0.0051 (17)
C16	0.030 (2)	0.040 (2)	0.0235 (19)	−0.0003 (18)	0.0037 (16)	0.0041 (17)
C17	0.028 (2)	0.048 (3)	0.038 (2)	0.0006 (19)	0.0021 (18)	0.007 (2)
C18	0.029 (2)	0.065 (3)	0.047 (3)	0.009 (2)	0.007 (2)	0.015 (2)
C19	0.041 (3)	0.063 (3)	0.047 (3)	0.021 (2)	0.011 (2)	0.005 (2)
C20	0.038 (2)	0.038 (2)	0.046 (3)	0.008 (2)	0.008 (2)	−0.004 (2)

S1—O3	1.445 (3)	C3—H3	0.9300
S1—O4	1.461 (3)	C4—C5	1.374 (6)
S1—O2	1.493 (3)	C4—H4	0.9300
S1—O1	1.509 (3)	C5—C6	1.480 (6)
S1—Ni1	2.6892 (13)	C6—C7	1.380 (6)
Ni1—N2	2.059 (3)	C7—C8	1.379 (6)
Ni1—N3	2.065 (3)	C7—H7	0.9300
Ni1—N4	2.070 (3)	C8—C9	1.372 (6)
Ni1—N1	2.075 (3)	C8—H8	0.9300
Ni1—O2	2.098 (3)	C9—C10	1.374 (6)
Ni1—O1	2.123 (3)	C9—H9	0.9300
O1W—H1W1	0.9753	C10—H10	0.9300
O1W—H2W1	0.8603	C11—C12	1.367 (6)
O2W—H1W2	0.9549	C11—H11	0.9300
O2W—H2W2	0.8500	C12—C13	1.376 (6)
O3W—H1W3	0.9888	C12—H12	0.9300
O3W—H2W3	0.8245	C13—C14	1.382 (6)
N1—C1	1.338 (5)	C13—H13	0.9300
N1—C5	1.347 (5)	C14—C15	1.380 (6)
N2—C10	1.335 (5)	C14—H14	0.9300
N2—C6	1.342 (5)	C15—C16	1.485 (6)
N3—C11	1.334 (5)	C16—C17	1.379 (6)
N3—C15	1.345 (5)	C17—C18	1.375 (6)
N4—C20	1.335 (5)	C17—H17	0.9300
N4—C16	1.352 (5)	C18—C19	1.349 (7)
C1—C2	1.362 (6)	C18—H18	0.9300
C1—H1	0.9300	C19—C20	1.379 (6)
C2—C3	1.372 (7)	C19—H19	0.9300
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.376 (6)
O3—S1—O4	112.5 (2)	C2—C3—C4	118.7 (4)
O3—S1—O2	111.38 (18)	C2—C3—H3	120.6
O4—S1—O2	109.64 (17)	C4—C3—H3	120.6
O3—S1—O1	110.62 (17)	C5—C4—C3	119.5 (4)
O4—S1—O1	109.38 (18)	C5—C4—H4	120.3
O2—S1—O1	102.89 (16)	C3—C4—H4	120.3
O3—S1—Ni1	125.58 (14)	N1—C5—C4	121.7 (4)
O4—S1—Ni1	121.92 (15)	N1—C5—C6	115.0 (3)
O2—S1—Ni1	50.95 (11)	C4—C5—C6	123.3 (4)
O1—S1—Ni1	51.94 (11)	N2—C6—C7	121.8 (4)
N2—Ni1—N3	171.54 (12)	N2—C6—C5	115.5 (3)
N2—Ni1—N4	93.94 (13)	C7—C6—C5	122.7 (4)
N3—Ni1—N4	79.32 (13)	C8—C7—C6	118.7 (4)
N2—Ni1—N1	78.92 (13)	C8—C7—H7	120.6
N3—Ni1—N1	96.65 (13)	C6—C7—H7	120.6
N4—Ni1—N1	96.66 (13)	C9—C8—C7	119.6 (4)
N2—Ni1—O2	96.16 (12)	C9—C8—H8	120.2
N3—Ni1—O2	91.51 (12)	C7—C8—H8	120.2
N4—Ni1—O2	164.38 (11)	C8—C9—C10	118.6 (4)
N1—Ni1—O2	96.95 (12)	C8—C9—H9	120.7
N2—Ni1—O1	91.50 (12)	C10—C9—H9	120.7
N3—Ni1—O1	94.73 (12)	N2—C10—C9	122.6 (4)
N4—Ni1—O1	100.34 (12)	N2—C10—H10	118.7
N1—Ni1—O1	161.03 (12)	C9—C10—H10	118.7
O2—Ni1—O1	67.57 (10)	N3—C11—C12	123.0 (4)
N2—Ni1—S1	94.37 (10)	N3—C11—H11	118.5
N3—Ni1—S1	93.99 (9)	C12—C11—H11	118.5
N4—Ni1—S1	133.72 (9)	C11—C12—C13	118.9 (4)
N1—Ni1—S1	129.62 (10)	C11—C12—H12	120.6
O2—Ni1—S1	33.54 (7)	C13—C12—H12	120.6
O1—Ni1—S1	34.03 (7)	C12—C13—C14	118.9 (4)
S1—O1—Ni1	94.03 (13)	C12—C13—H13	120.5
S1—O2—Ni1	95.51 (13)	C14—C13—H13	120.5
H1W1—O1W—H2W1	89.2	C15—C14—C13	119.1 (4)
H1W2—O2W—H2W2	110.8	C15—C14—H14	120.4
H1W3—O3W—H2W3	104.2	C13—C14—H14	120.4
C1—N1—C5	118.0 (4)	N3—C15—C14	121.6 (4)
C1—N1—Ni1	127.0 (3)	N3—C15—C16	115.4 (3)
C5—N1—Ni1	115.0 (3)	C14—C15—C16	123.0 (4)
C10—N2—C6	118.7 (3)	N4—C16—C17	122.0 (4)
C10—N2—Ni1	125.8 (3)	N4—C16—C15	115.2 (3)
C6—N2—Ni1	115.4 (3)	C17—C16—C15	122.7 (4)
C11—N3—C15	118.5 (3)	C18—C17—C16	119.0 (4)
C11—N3—Ni1	126.4 (3)	C18—C17—H17	120.5
C15—N3—Ni1	115.1 (3)	C16—C17—H17	120.5
C20—N4—C16	117.1 (3)	C19—C18—C17	119.7 (4)
C20—N4—Ni1	127.9 (3)	C19—C18—H18	120.1
C16—N4—Ni1	114.8 (3)	C17—C18—H18	120.1
N1—C1—C2	123.0 (4)	C18—C19—C20	118.6 (4)
N1—C1—H1	118.5	C18—C19—H19	120.7
C2—C1—H1	118.5	C20—C19—H19	120.7
C1—C2—C3	119.1 (4)	N4—C20—C19	123.5 (4)
C1—C2—H2	120.5	N4—C20—H20	118.2
C3—C2—H2	120.5	C19—C20—H20	118.2
O3—S1—Ni1—N2	175.62 (18)	N4—Ni1—N3—C15	1.3 (3)
O4—S1—Ni1—N2	−4.30 (19)	N1—Ni1—N3—C15	−94.2 (3)
O2—S1—Ni1—N2	−94.56 (16)	O2—Ni1—N3—C15	168.6 (3)
O1—S1—Ni1—N2	86.20 (16)	O1—Ni1—N3—C15	101.0 (3)
O3—S1—Ni1—N3	−3.11 (18)	S1—Ni1—N3—C15	135.1 (3)
O4—S1—Ni1—N3	176.96 (18)	N2—Ni1—N4—C20	−8.9 (4)
O2—S1—Ni1—N3	86.71 (16)	N3—Ni1—N4—C20	176.3 (4)
O1—S1—Ni1—N3	−92.54 (16)	N1—Ni1—N4—C20	−88.2 (3)
O3—S1—Ni1—N4	75.9 (2)	O2—Ni1—N4—C20	121.3 (5)
O4—S1—Ni1—N4	−104.0 (2)	O1—Ni1—N4—C20	83.3 (3)
O2—S1—Ni1—N4	165.74 (18)	S1—Ni1—N4—C20	91.0 (3)
O1—S1—Ni1—N4	−13.50 (18)	N2—Ni1—N4—C16	176.2 (3)
O3—S1—Ni1—N1	−105.1 (2)	N3—Ni1—N4—C16	1.3 (3)
O4—S1—Ni1—N1	74.9 (2)	N1—Ni1—N4—C16	96.9 (3)
O2—S1—Ni1—N1	−15.33 (18)	O2—Ni1—N4—C16	−53.6 (5)
O1—S1—Ni1—N1	165.43 (17)	O1—Ni1—N4—C16	−91.6 (3)
O3—S1—Ni1—O2	−89.8 (2)	S1—Ni1—N4—C16	−83.9 (3)
O4—S1—Ni1—O2	90.3 (2)	C5—N1—C1—C2	−0.7 (7)
O1—S1—Ni1—O2	−179.24 (19)	Ni1—N1—C1—C2	−179.1 (4)
O3—S1—Ni1—O1	89.4 (2)	N1—C1—C2—C3	−1.0 (8)
O4—S1—Ni1—O1	−90.5 (2)	C1—C2—C3—C4	1.8 (7)
O2—S1—Ni1—O1	179.24 (19)	C2—C3—C4—C5	−1.0 (7)
O3—S1—O1—Ni1	−119.66 (17)	C1—N1—C5—C4	1.6 (6)
O4—S1—O1—Ni1	115.88 (17)	Ni1—N1—C5—C4	−179.9 (3)
O2—S1—O1—Ni1	−0.60 (15)	C1—N1—C5—C6	−176.7 (4)
N2—Ni1—O1—S1	−95.60 (15)	Ni1—N1—C5—C6	1.8 (4)
N3—Ni1—O1—S1	90.14 (14)	C3—C4—C5—N1	−0.7 (6)
N4—Ni1—O1—S1	170.12 (13)	C3—C4—C5—C6	177.4 (4)
N1—Ni1—O1—S1	−36.6 (4)	C10—N2—C6—C7	0.6 (6)
O2—Ni1—O1—S1	0.45 (11)	Ni1—N2—C6—C7	177.2 (3)
O3—S1—O2—Ni1	119.14 (16)	C10—N2—C6—C5	−179.9 (3)
O4—S1—O2—Ni1	−115.69 (18)	Ni1—N2—C6—C5	−3.3 (4)
O1—S1—O2—Ni1	0.61 (15)	N1—C5—C6—N2	1.0 (5)
N2—Ni1—O2—S1	88.62 (15)	C4—C5—C6—N2	−177.3 (4)
N3—Ni1—O2—S1	−94.95 (14)	N1—C5—C6—C7	−179.5 (4)
N4—Ni1—O2—S1	−41.4 (5)	C4—C5—C6—C7	2.2 (6)
N1—Ni1—O2—S1	168.16 (14)	N2—C6—C7—C8	−0.7 (6)
O1—Ni1—O2—S1	−0.46 (11)	C5—C6—C7—C8	179.9 (4)
N2—Ni1—N1—C1	175.7 (4)	C6—C7—C8—C9	−0.3 (7)
N3—Ni1—N1—C1	−11.6 (4)	C7—C8—C9—C10	1.3 (7)
N4—Ni1—N1—C1	−91.6 (4)	C6—N2—C10—C9	0.5 (6)
O2—Ni1—N1—C1	80.7 (4)	Ni1—N2—C10—C9	−175.7 (3)
O1—Ni1—N1—C1	114.8 (4)	C8—C9—C10—N2	−1.5 (7)
S1—Ni1—N1—C1	89.2 (4)	C15—N3—C11—C12	2.3 (6)
N2—Ni1—N1—C5	−2.7 (3)	Ni1—N3—C11—C12	−176.9 (3)
N3—Ni1—N1—C5	170.0 (3)	N3—C11—C12—C13	−0.8 (6)
N4—Ni1—N1—C5	90.0 (3)	C11—C12—C13—C14	−1.1 (7)
O2—Ni1—N1—C5	−97.7 (3)	C12—C13—C14—C15	1.3 (7)
O1—Ni1—N1—C5	−63.5 (5)	C11—N3—C15—C14	−2.0 (6)
S1—Ni1—N1—C5	−89.2 (3)	Ni1—N3—C15—C14	177.2 (3)
N3—Ni1—N2—C10	120.5 (8)	C11—N3—C15—C16	177.2 (3)
N4—Ni1—N2—C10	83.6 (3)	Ni1—N3—C15—C16	−3.5 (4)
N1—Ni1—N2—C10	179.6 (4)	C13—C14—C15—N3	0.2 (6)
O2—Ni1—N2—C10	−84.5 (3)	C13—C14—C15—C16	−178.9 (4)
O1—Ni1—N2—C10	−16.9 (3)	C20—N4—C16—C17	−1.3 (6)
S1—Ni1—N2—C10	−50.8 (3)	Ni1—N4—C16—C17	174.2 (3)
N3—Ni1—N2—C6	−55.8 (9)	C20—N4—C16—C15	−179.0 (3)
N4—Ni1—N2—C6	−92.8 (3)	Ni1—N4—C16—C15	−3.5 (4)
N1—Ni1—N2—C6	3.3 (3)	N3—C15—C16—N4	4.7 (5)
O2—Ni1—N2—C6	99.2 (3)	C14—C15—C16—N4	−176.1 (4)
O1—Ni1—N2—C6	166.8 (3)	N3—C15—C16—C17	−173.0 (4)
S1—Ni1—N2—C6	132.8 (3)	C14—C15—C16—C17	6.2 (6)
N2—Ni1—N3—C11	142.9 (7)	N4—C16—C17—C18	0.5 (6)
N4—Ni1—N3—C11	−179.5 (3)	C15—C16—C17—C18	178.0 (4)
N1—Ni1—N3—C11	84.9 (3)	C16—C17—C18—C19	0.9 (7)
O2—Ni1—N3—C11	−12.2 (3)	C17—C18—C19—C20	−1.3 (7)
O1—Ni1—N3—C11	−79.8 (3)	C16—N4—C20—C19	0.9 (6)
S1—Ni1—N3—C11	−45.7 (3)	Ni1—N4—C20—C19	−173.9 (3)
N2—Ni1—N3—C15	−36.3 (9)	C18—C19—C20—N4	0.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1i	0.98	1.99	2.925 (5)	160
O1W—H2W1···O4ii	0.86	2.04	2.819 (5)	150
O2W—H1W2···O3Wiii	0.95	2.08	3.03 (2)	174
O2W—H2W2···O1W	0.85	1.93	2.774 (11)	170
O3W—H1W3···O3Wiv	0.99	1.91	2.86 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O1i	0.98	1.99	2.925 (5)	160
O1W—H2W1⋯O4ii	0.86	2.04	2.819 (5)	150
O2W—H1W2⋯O3W iii	0.95	2.08	3.03 (2)	174
O2W—H2W2⋯O1W	0.85	1.93	2.774 (11)	170
O3W—H1W3⋯O3W iv	0.99	1.91	2.86 (4)	163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .