(Acetato-κO)(aqua-κO)(2-{bis-[(3,5-dimethyl-1H-pyrazol-1-yl-κN(2))methyl]amino-κN}ethanol-κO)nickel(II) perchlorate monohydrate.

In the structure of the title complex, [Ni(CH(3)CO(2))(C(14)H(23)N(5)O)(H(2)O)]ClO(4)·H(2)O, the Ni(II) centre has a distorted octa-hedral environment defined by one O and three N atoms derived from the tetra-dentate ligand, and two O atoms, one from a water mol-ecule and the other from an acetate anion. The mol-ecules are connected into a three-dimensional architecture by O-H⋯O hydrogen bonds. The perchlorate anion is disordered over two positions; the major component has a site-occupancy factor of 0.525 (19).

Related literature

For the preparation of the tripodal ligand, see: Malachowski et al. (1992 ▶). For background to hydrolytic enzymes, see: Koike et al. (1995 ▶); Lipscomb & Sträter (1996 ▶). For related structures, see: Shin et al. (2011 ▶); Sundaravel et al. (2011 ▶); Xia et al. (2001 ▶).

Experimental

Crystal data

[Ni(C2H3O2)(C14H23N5O)(H2O)]ClO4·H2O

M = 530.61

Monoclinic,

a = 9.6055 (11) Å

b = 9.9889 (11) Å

c = 24.258 (3) Å

β = 90.284 (2)°

V = 2327.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.00 mm−1

T = 293 K

0.43 × 0.37 × 0.21 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 2003 ▶) T min = 0.732, T max = 1.000

13249 measured reflections

5057 independent reflections

2284 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.142

S = 0.82

5057 reflections

310 parameters

26 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.50 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007970/tk5060sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007970/tk5060Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007970/tk5060Isup3.mol

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

[Ni(C2H3O2)(C14H23N5O)(H2O)]ClO4·H2O	F(000) = 1112
Mr = 530.61	Dx = 1.514 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1110 reflections
a = 9.6055 (11) Å	θ = 5.3°
b = 9.9889 (11) Å	µ = 1.00 mm−1
c = 24.258 (3) Å	T = 293 K
β = 90.284 (2)°	Block, blue
V = 2327.5 (5) Å3	0.43 × 0.37 × 0.21 mm
Z = 4

Bruker APEX CCD diffractometer	5057 independent reflections
Radiation source: fine-focus sealed tube	2284 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
φ and ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 2003)	h = −12→12
Tmin = 0.732, Tmax = 1.000	k = −9→12
13249 measured reflections	l = −30→24

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 0.82	w = 1/[σ2(Fo2) + (0.0493P)2] where P = (Fo2 + 2Fc2)/3
5057 reflections	(Δ/σ)max = 0.001
310 parameters	Δρmax = 0.66 e Å−3
26 restraints	Δρmin = −0.50 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	Occ. (<1)
Ni	−0.44003 (7)	1.26474 (6)	0.84018 (3)	0.0315 (2)
Cl	−0.00311 (17)	0.76885 (16)	0.95183 (7)	0.0575 (4)	0.525 (19)
Cl'	−0.00311 (17)	0.76885 (16)	0.95183 (7)	0.0575 (4)	0.475 (19)
N1	−0.2854 (4)	1.2368 (4)	0.90201 (15)	0.0328 (10)
N2	−0.2798 (4)	1.1888 (4)	0.79269 (17)	0.0342 (10)
N3	−0.1741 (4)	1.1411 (4)	0.82475 (17)	0.0355 (10)
N4	−0.5531 (5)	1.3175 (4)	0.90797 (17)	0.0374 (11)
N5	−0.4845 (5)	1.2870 (4)	0.95579 (18)	0.0436 (12)
O1	−0.3473 (4)	1.4547 (3)	0.83710 (15)	0.0383 (9)
H26	−0.357 (6)	1.491 (5)	0.8051 (10)	0.07 (2)*
O2	−0.5772 (3)	1.3140 (3)	0.78136 (14)	0.0383 (9)
O3	−0.6299 (4)	1.1117 (3)	0.74957 (14)	0.0437 (9)
O4	−0.5166 (4)	1.0662 (4)	0.84915 (19)	0.0434 (9)
H27	−0.572 (4)	1.067 (5)	0.8766 (14)	0.050 (19)*
H28	−0.565 (5)	1.062 (6)	0.8195 (14)	0.08 (2)*
O5	0.2962 (5)	1.0394 (6)	0.9409 (2)	0.0831 (15)
H29	0.240 (5)	0.972 (4)	0.938 (2)	0.09 (3)*
H30	0.276 (6)	1.100 (4)	0.965 (2)	0.08 (3)*
O11	0.1400 (8)	0.7866 (11)	0.9351 (5)	0.088 (3)	0.525 (19)
O11'	0.1098 (13)	0.8400 (14)	0.9279 (5)	0.106 (3)	0.475 (19)
O12	−0.0120 (12)	0.7935 (11)	1.0102 (3)	0.088 (3)	0.525 (19)
O12'	−0.0278 (16)	0.8426 (13)	1.0018 (4)	0.106 (3)	0.475 (19)
O13	−0.1096 (9)	0.8469 (13)	0.9288 (5)	0.088 (3)	0.525 (19)
O13'	−0.1122 (10)	0.7788 (18)	0.9127 (5)	0.106 (3)	0.475 (19)
O14	−0.0262 (12)	0.6290 (7)	0.9444 (5)	0.088 (3)	0.525 (19)
O14'	0.0112 (16)	0.6299 (8)	0.9658 (6)	0.106 (3)	0.475 (19)
C1	−0.1981 (6)	1.1237 (5)	0.8832 (2)	0.0438 (14)
H1A	−0.1102	1.1230	0.9030	0.053*
H1B	−0.2452	1.0394	0.8899	0.053*
C2	−0.0605 (6)	1.1114 (5)	0.7946 (2)	0.0459 (15)
C3	−0.0943 (6)	1.1418 (5)	0.7411 (2)	0.0482 (16)
H3A	−0.0374	1.1314	0.7105	0.058*
C4	−0.2312 (6)	1.1917 (5)	0.7410 (2)	0.0409 (14)
C5	−0.3171 (6)	1.2402 (5)	0.6948 (2)	0.0535 (16)
H5A	−0.4067	1.2672	0.7083	0.080*
H5B	−0.3287	1.1698	0.6683	0.080*
H5C	−0.2721	1.3152	0.6778	0.080*
C6	0.0674 (6)	1.0516 (6)	0.8194 (3)	0.072 (2)
H6A	0.0559	1.0437	0.8585	0.107*
H6B	0.1458	1.1081	0.8118	0.107*
H6C	0.0829	0.9646	0.8038	0.107*
C7	−0.3614 (6)	1.2020 (5)	0.9529 (2)	0.0475 (15)
H7A	−0.3885	1.1084	0.9522	0.057*
H7B	−0.3024	1.2166	0.9850	0.057*
C8	−0.5593 (7)	1.3211 (6)	1.0010 (2)	0.0497 (16)
C9	−0.6788 (7)	1.3771 (5)	0.9807 (2)	0.0536 (17)
H9A	−0.7517	1.4113	1.0014	0.064*
C10	−0.6722 (6)	1.3739 (5)	0.9235 (2)	0.0442 (15)
C11	−0.7764 (6)	1.4210 (5)	0.8818 (3)	0.0629 (18)
H11B	−0.7416	1.4047	0.8454	0.094*
H11C	−0.7923	1.5152	0.8866	0.094*
H11D	−0.8623	1.3734	0.8867	0.094*
C12	−0.5118 (7)	1.2947 (6)	1.0577 (2)	0.078 (2)
H12A	−0.4213	1.2540	1.0569	0.117*
H12B	−0.5761	1.2354	1.0755	0.117*
H12C	−0.5070	1.3774	1.0778	0.117*
C13	−0.2072 (6)	1.3644 (5)	0.9084 (2)	0.0425 (14)
H13A	−0.1120	1.3446	0.9191	0.051*
H13B	−0.2490	1.4167	0.9377	0.051*
C14	−0.2067 (6)	1.4462 (5)	0.8560 (2)	0.0424 (14)
H14A	−0.1700	1.5350	0.8632	0.051*
H14B	−0.1491	1.4035	0.8284	0.051*
C15	−0.6364 (5)	1.2371 (5)	0.7480 (2)	0.0351 (12)
C16	−0.7201 (6)	1.3043 (5)	0.7039 (2)	0.0552 (16)
H16A	−0.7145	1.3996	0.7084	0.083*
H16B	−0.8155	1.2763	0.7064	0.083*
H16C	−0.6840	1.2800	0.6684	0.083*

	U11	U22	U33	U12	U13	U23
Ni	0.0311 (4)	0.0329 (4)	0.0304 (4)	0.0005 (3)	−0.0002 (3)	−0.0012 (3)
Cl	0.0533 (10)	0.0626 (11)	0.0566 (10)	−0.0156 (8)	−0.0060 (8)	0.0043 (9)
Cl'	0.0533 (10)	0.0626 (11)	0.0566 (10)	−0.0156 (8)	−0.0060 (8)	0.0043 (9)
N1	0.037 (3)	0.032 (2)	0.029 (2)	−0.003 (2)	−0.0011 (19)	0.0008 (19)
N2	0.031 (3)	0.039 (2)	0.032 (3)	0.0024 (19)	0.000 (2)	−0.0026 (19)
N3	0.029 (3)	0.041 (3)	0.036 (3)	0.005 (2)	−0.002 (2)	0.001 (2)
N4	0.039 (3)	0.039 (2)	0.034 (3)	−0.001 (2)	0.003 (2)	0.000 (2)
N5	0.051 (3)	0.044 (3)	0.036 (3)	−0.008 (2)	0.012 (2)	−0.003 (2)
O1	0.037 (2)	0.036 (2)	0.042 (2)	−0.0039 (16)	−0.0077 (19)	0.0048 (18)
O2	0.039 (2)	0.036 (2)	0.040 (2)	0.0020 (16)	−0.0108 (18)	−0.0072 (17)
O3	0.052 (3)	0.034 (2)	0.045 (2)	−0.0001 (17)	−0.0064 (19)	−0.0017 (17)
O4	0.042 (3)	0.044 (2)	0.045 (3)	−0.0032 (18)	−0.003 (2)	0.001 (2)
O5	0.084 (4)	0.073 (4)	0.092 (4)	−0.034 (3)	0.006 (3)	0.006 (3)
O11	0.086 (5)	0.067 (4)	0.109 (5)	0.005 (3)	−0.015 (3)	0.000 (3)
O11'	0.118 (7)	0.093 (6)	0.106 (6)	−0.028 (4)	−0.013 (4)	0.003 (4)
O12	0.086 (5)	0.067 (4)	0.109 (5)	0.005 (3)	−0.015 (3)	0.000 (3)
O12'	0.118 (7)	0.093 (6)	0.106 (6)	−0.028 (4)	−0.013 (4)	0.003 (4)
O13	0.086 (5)	0.067 (4)	0.109 (5)	0.005 (3)	−0.015 (3)	0.000 (3)
O13'	0.118 (7)	0.093 (6)	0.106 (6)	−0.028 (4)	−0.013 (4)	0.003 (4)
O14	0.086 (5)	0.067 (4)	0.109 (5)	0.005 (3)	−0.015 (3)	0.000 (3)
O14'	0.118 (7)	0.093 (6)	0.106 (6)	−0.028 (4)	−0.013 (4)	0.003 (4)
C1	0.047 (4)	0.042 (3)	0.043 (4)	0.008 (3)	−0.008 (3)	0.001 (3)
C2	0.036 (4)	0.046 (3)	0.056 (4)	0.000 (3)	0.009 (3)	−0.004 (3)
C3	0.036 (4)	0.052 (4)	0.056 (4)	0.001 (3)	0.019 (3)	−0.006 (3)
C4	0.046 (4)	0.037 (3)	0.040 (4)	−0.004 (3)	0.008 (3)	−0.005 (3)
C5	0.054 (4)	0.078 (4)	0.029 (3)	0.002 (3)	0.007 (3)	0.003 (3)
C6	0.039 (4)	0.081 (5)	0.095 (6)	0.014 (3)	0.005 (4)	0.011 (4)
C7	0.059 (4)	0.052 (4)	0.031 (3)	−0.001 (3)	−0.004 (3)	0.006 (3)
C8	0.059 (5)	0.053 (4)	0.037 (4)	−0.017 (3)	0.018 (3)	−0.009 (3)
C9	0.051 (4)	0.054 (4)	0.055 (4)	−0.012 (3)	0.027 (4)	−0.020 (3)
C10	0.044 (4)	0.030 (3)	0.058 (4)	−0.011 (3)	0.018 (3)	−0.011 (3)
C11	0.039 (4)	0.057 (4)	0.092 (5)	0.008 (3)	0.009 (4)	−0.014 (4)
C12	0.103 (6)	0.096 (5)	0.036 (4)	−0.014 (4)	0.020 (4)	−0.008 (3)
C13	0.046 (4)	0.042 (3)	0.040 (3)	−0.007 (3)	−0.004 (3)	−0.006 (3)
C14	0.044 (4)	0.041 (3)	0.042 (4)	−0.007 (3)	−0.010 (3)	0.003 (3)
C15	0.028 (3)	0.045 (3)	0.033 (3)	0.001 (3)	0.002 (2)	0.002 (3)
C16	0.051 (4)	0.055 (4)	0.059 (4)	0.000 (3)	−0.021 (3)	0.002 (3)

Ni—O2	1.999 (3)	C2—C6	1.490 (7)
Ni—N4	2.044 (4)	C3—C4	1.406 (7)
Ni—N2	2.071 (4)	C3—H3A	0.9300
Ni—O1	2.097 (3)	C4—C5	1.471 (7)
Ni—N1	2.124 (4)	C5—H5A	0.9600
Ni—O4	2.126 (4)	C5—H5B	0.9600
Cl—O13	1.401 (7)	C5—H5C	0.9600
Cl—O14	1.426 (7)	C6—H6A	0.9600
Cl—O12	1.439 (7)	C6—H6B	0.9600
Cl—O11	1.446 (7)	C6—H6C	0.9600
N1—C7	1.480 (6)	C7—H7A	0.9700
N1—C1	1.481 (6)	C7—H7B	0.9700
N1—C13	1.487 (6)	C8—C9	1.368 (8)
N2—C4	1.339 (6)	C8—C12	1.471 (8)
N2—N3	1.362 (5)	C9—C10	1.389 (7)
N3—C2	1.349 (6)	C9—H9A	0.9300
N3—C1	1.447 (6)	C10—C11	1.495 (7)
N4—C10	1.332 (6)	C11—H11B	0.9600
N4—N5	1.366 (5)	C11—H11C	0.9600
N5—C8	1.358 (6)	C11—H11D	0.9600
N5—C7	1.458 (6)	C12—H12A	0.9600
O1—C14	1.427 (6)	C12—H12B	0.9600
O1—H26	0.863 (10)	C12—H12C	0.9600
O2—C15	1.251 (6)	C13—C14	1.512 (6)
O3—C15	1.255 (5)	C13—H13A	0.9700
O4—H27	0.858 (10)	C13—H13B	0.9700
O4—H28	0.856 (10)	C14—H14A	0.9700
O5—H29	0.861 (10)	C14—H14B	0.9700
O5—H30	0.862 (10)	C15—C16	1.494 (7)
C1—H1A	0.9700	C16—H16A	0.9600
C1—H1B	0.9700	C16—H16B	0.9600
C2—C3	1.371 (7)	C16—H16C	0.9600
O2—Ni—N4	99.19 (16)	C3—C4—C5	129.7 (5)
O2—Ni—N2	100.50 (15)	C4—C5—H5A	109.5
N4—Ni—N2	160.25 (17)	C4—C5—H5B	109.5
O2—Ni—O1	91.73 (14)	H5A—C5—H5B	109.5
N4—Ni—O1	91.29 (15)	C4—C5—H5C	109.5
N2—Ni—O1	89.70 (15)	H5A—C5—H5C	109.5
O2—Ni—N1	172.99 (14)	H5B—C5—H5C	109.5
N4—Ni—N1	80.69 (16)	C2—C6—H6A	109.5
N2—Ni—N1	79.96 (16)	C2—C6—H6B	109.5
O1—Ni—N1	81.27 (14)	H6A—C6—H6B	109.5
O2—Ni—O4	94.35 (15)	C2—C6—H6C	109.5
N4—Ni—O4	88.45 (16)	H6A—C6—H6C	109.5
N2—Ni—O4	88.49 (16)	H6B—C6—H6C	109.5
O1—Ni—O4	173.88 (16)	N5—C7—N1	107.8 (4)
N1—Ni—O4	92.65 (16)	N5—C7—H7A	110.1
O13—Cl—O14	112.4 (5)	N1—C7—H7A	110.1
O13—Cl—O12	104.5 (6)	N5—C7—H7B	110.1
O14—Cl—O12	106.4 (5)	N1—C7—H7B	110.1
O13—Cl—O11	120.9 (6)	H7A—C7—H7B	108.5
O14—Cl—O11	103.4 (6)	N5—C8—C9	104.9 (5)
O12—Cl—O11	108.4 (7)	N5—C8—C12	123.3 (6)
C7—N1—C1	111.1 (4)	C9—C8—C12	131.9 (6)
C7—N1—C13	111.4 (4)	C8—C9—C10	108.0 (5)
C1—N1—C13	113.6 (4)	C8—C9—H9A	126.0
C7—N1—Ni	105.9 (3)	C10—C9—H9A	126.0
C1—N1—Ni	106.1 (3)	N4—C10—C9	109.6 (6)
C13—N1—Ni	108.2 (3)	N4—C10—C11	121.0 (5)
C4—N2—N3	106.2 (4)	C9—C10—C11	129.4 (5)
C4—N2—Ni	140.9 (4)	C10—C11—H11B	109.5
N3—N2—Ni	111.4 (3)	C10—C11—H11C	109.5
C2—N3—N2	111.7 (4)	H11B—C11—H11C	109.5
C2—N3—C1	129.6 (5)	C10—C11—H11D	109.5
N2—N3—C1	118.6 (4)	H11B—C11—H11D	109.5
C10—N4—N5	105.4 (4)	H11C—C11—H11D	109.5
C10—N4—Ni	142.9 (4)	C8—C12—H12A	109.5
N5—N4—Ni	111.7 (3)	C8—C12—H12B	109.5
C8—N5—N4	112.1 (5)	H12A—C12—H12B	109.5
C8—N5—C7	128.1 (5)	C8—C12—H12C	109.5
N4—N5—C7	118.5 (4)	H12A—C12—H12C	109.5
C14—O1—Ni	109.7 (3)	H12B—C12—H12C	109.5
C14—O1—H26	114 (4)	N1—C13—C14	112.3 (4)
Ni—O1—H26	112 (4)	N1—C13—H13A	109.2
C15—O2—Ni	127.3 (3)	C14—C13—H13A	109.2
Ni—O4—H27	107 (3)	N1—C13—H13B	109.2
Ni—O4—H28	99 (4)	C14—C13—H13B	109.2
H27—O4—H28	108 (5)	H13A—C13—H13B	107.9
H29—O5—H30	117 (3)	O1—C14—C13	107.2 (4)
N3—C1—N1	107.7 (4)	O1—C14—H14A	110.3
N3—C1—H1A	110.2	C13—C14—H14A	110.3
N1—C1—H1A	110.2	O1—C14—H14B	110.3
N3—C1—H1B	110.2	C13—C14—H14B	110.3
N1—C1—H1B	110.2	H14A—C14—H14B	108.5
H1A—C1—H1B	108.5	O2—C15—O3	124.8 (5)
N3—C2—C3	106.0 (5)	O2—C15—C16	115.4 (5)
N3—C2—C6	122.5 (5)	O3—C15—C16	119.8 (5)
C3—C2—C6	131.5 (5)	C15—C16—H16A	109.5
C2—C3—C4	107.3 (5)	C15—C16—H16B	109.5
C2—C3—H3A	126.4	H16A—C16—H16B	109.5
C4—C3—H3A	126.4	C15—C16—H16C	109.5
N2—C4—C3	108.8 (5)	H16A—C16—H16C	109.5
N2—C4—C5	121.5 (5)	H16B—C16—H16C	109.5
O2—Ni—N1—C7	118.3 (11)	O4—Ni—O1—C14	18.1 (16)
N4—Ni—N1—C7	28.7 (3)	N4—Ni—O2—C15	−115.7 (4)
N2—Ni—N1—C7	−147.3 (3)	N2—Ni—O2—C15	62.7 (4)
O1—Ni—N1—C7	121.4 (3)	O1—Ni—O2—C15	152.7 (4)
O4—Ni—N1—C7	−59.3 (3)	N1—Ni—O2—C15	155.8 (11)
O2—Ni—N1—C1	−123.5 (11)	O4—Ni—O2—C15	−26.6 (4)
N4—Ni—N1—C1	146.9 (3)	C2—N3—C1—N1	145.0 (5)
N2—Ni—N1—C1	−29.1 (3)	N2—N3—C1—N1	−38.1 (6)
O1—Ni—N1—C1	−120.4 (3)	C7—N1—C1—N3	157.0 (4)
O4—Ni—N1—C1	58.9 (3)	C13—N1—C1—N3	−76.5 (5)
O2—Ni—N1—C13	−1.3 (13)	Ni—N1—C1—N3	42.3 (4)
N4—Ni—N1—C13	−90.9 (3)	N2—N3—C2—C3	0.3 (6)
N2—Ni—N1—C13	93.1 (3)	C1—N3—C2—C3	177.3 (5)
O1—Ni—N1—C13	1.9 (3)	N2—N3—C2—C6	−177.1 (5)
O4—Ni—N1—C13	−178.9 (3)	C1—N3—C2—C6	−0.1 (8)
O2—Ni—N2—C4	20.1 (6)	N3—C2—C3—C4	0.6 (6)
N4—Ni—N2—C4	−164.6 (5)	C6—C2—C3—C4	177.7 (6)
O1—Ni—N2—C4	−71.6 (5)	N3—N2—C4—C3	1.4 (5)
N1—Ni—N2—C4	−152.8 (6)	Ni—N2—C4—C3	165.0 (4)
O4—Ni—N2—C4	114.2 (5)	N3—N2—C4—C5	−179.1 (4)
O2—Ni—N2—N3	−176.8 (3)	Ni—N2—C4—C5	−15.5 (8)
N4—Ni—N2—N3	−1.5 (6)	C2—C3—C4—N2	−1.3 (6)
O1—Ni—N2—N3	91.5 (3)	C2—C3—C4—C5	179.3 (5)
N1—Ni—N2—N3	10.3 (3)	C8—N5—C7—N1	−157.5 (5)
O4—Ni—N2—N3	−82.7 (3)	N4—N5—C7—N1	36.8 (6)
C4—N2—N3—C2	−1.1 (5)	C1—N1—C7—N5	−155.8 (4)
Ni—N2—N3—C2	−170.1 (3)	C13—N1—C7—N5	76.5 (5)
C4—N2—N3—C1	−178.5 (4)	Ni—N1—C7—N5	−41.0 (4)
Ni—N2—N3—C1	12.5 (5)	N4—N5—C8—C9	−0.9 (6)
O2—Ni—N4—C10	−4.3 (6)	C7—N5—C8—C9	−167.4 (5)
N2—Ni—N4—C10	−179.7 (5)	N4—N5—C8—C12	177.7 (5)
O1—Ni—N4—C10	87.6 (6)	C7—N5—C8—C12	11.2 (8)
N1—Ni—N4—C10	168.6 (6)	N5—C8—C9—C10	0.4 (6)
O4—Ni—N4—C10	−98.5 (6)	C12—C8—C9—C10	−178.0 (6)
O2—Ni—N4—N5	176.8 (3)	N5—N4—C10—C9	−0.7 (5)
N2—Ni—N4—N5	1.4 (6)	Ni—N4—C10—C9	−179.7 (4)
O1—Ni—N4—N5	−91.3 (3)	N5—N4—C10—C11	−179.9 (4)
N1—Ni—N4—N5	−10.3 (3)	Ni—N4—C10—C11	1.2 (8)
O4—Ni—N4—N5	82.6 (3)	C8—C9—C10—N4	0.2 (6)
C10—N4—N5—C8	1.0 (5)	C8—C9—C10—C11	179.2 (5)
Ni—N4—N5—C8	−179.6 (3)	C7—N1—C13—C14	−143.8 (4)
C10—N4—N5—C7	169.0 (4)	C1—N1—C13—C14	89.8 (5)
Ni—N4—N5—C7	−11.7 (5)	Ni—N1—C13—C14	−27.7 (5)
O2—Ni—O1—C14	−155.1 (3)	Ni—O1—C14—C13	−46.3 (4)
N4—Ni—O1—C14	105.7 (3)	N1—C13—C14—O1	49.7 (5)
N2—Ni—O1—C14	−54.6 (3)	Ni—O2—C15—O3	7.7 (7)
N1—Ni—O1—C14	25.3 (3)	Ni—O2—C15—C16	−172.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H26···O3i	0.86 (1)	1.80 (1)	2.631 (10)	163 (1)
O4—H27···O5ii	0.86 (1)	2.03 (1)	2.882 (10)	171 (1)
O4—H28···O3	0.86 (1)	1.87 (1)	2.684 (10)	158 (5)
O5—H29···O11′	0.86 (1)	1.84 (1)	2.695 (10)	174 (1)
O5—H29···O11	0.86 (1)	2.09 (1)	2.940 (10)	168 (1)
O5—H30···O12′iii	0.86 (1)	2.59 (1)	3.162 (10)	125 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H26⋯O3i	0.86 (1)	1.80 (1)	2.631 (10)	163 (1)
O4—H27⋯O5ii	0.86 (1)	2.03 (1)	2.882 (10)	171 (1)
O4—H28⋯O3	0.86 (1)	1.87 (1)	2.684 (10)	158 (5)
O5—H29⋯O11′	0.86 (1)	1.84 (1)	2.695 (10)	174 (1)
O5—H29⋯O11	0.86 (1)	2.09 (1)	2.940 (10)	168 (1)
O5—H30⋯O12′iii	0.86 (1)	2.59 (1)	3.162 (10)	125 (1)

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