Bis(6'-carb-oxy-2,2'-bipyridine-6-carboxyl-ato-κN,N',O)nickel(II) tetra-hydrate.

In the title compound, [Ni(C(12)H(7)N(2)O(4))(2)]·4H(2)O, the Ni atom is located at the centre of a distorted octa-hedron, formed by four N atoms and two O atoms from the same two tridentating chelated 6-carb-oxy-2,2'-bipyridine-6'-carboxyl-ate (L) ligands. Face-to-face π-stacking inter-actions between inversion-related pyridine rings with centroid-centroid distances of 3.548 (3) and 3.662 (3) Å (perpendicular distances between the respective rings are 3.314 and 3.438 Å) are found. Inter-molecular O-H⋯O hydrogen bonds between water mol-ecules and L ligands form R(5) (3)(10), R(6) (5)(14) and R(5) (5)(12) rings and also a centrosymmetric cage-like unit of water mol-ecules, which link eight adjacent Ni(II) centers, forming a three-dimensional framework.

Related literature

For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶). For the structural and photophysical properties of LnIII complexes with the title ligand, see: Bünzli et al. (2000 ▶). For a catena-poly diaqua CdII complex with the title ligand, see: Knight et al. (2006 ▶). For an explanation of ‘ligand star’, see: Gao et al. (2006 ▶). For the structural characterization and fluorescent properties of LnIII complexes with pyridine-2,6-dicarboxylic acid, see: Liu et al. (2008 ▶). For the structural and photophysical properties of EuIII complexes with 2,2′-dipyridine-4, 4′-dicarboxylic acid, see: Law et al. (2007 ▶). For the structural properties of a metal-organic framework (MOF) based on Pt, Y and 2,2′-bipyridine-5,5′-dicarboxyl­ate, see: Szeto et al. (2006 ▶). For a review of the properties of coordination polymer networks via O– and N-atoms, see: Robin & Fromm (2006 ▶).

Experimental

Crystal data

[Ni(C12H7N2O4)2]·4H2O

M = 617.17

Triclinic,

a = 9.990 (2) Å

b = 10.896 (2) Å

c = 12.565 (3) Å

α = 112.97 (3)°

β = 100.09 (3)°

γ = 90.30 (3)°

V = 1235.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.86 mm−1

T = 113 K

0.20 × 0.10 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.846, T max = 0.934

7165 measured reflections

4305 independent reflections

2745 reflections with I > 2σ(I)

R int = 0.126

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.211

S = 1.05

4305 reflections

372 parameters

H-atom parameters constrained

Δρmax = 0.96 e Å−3

Δρmin = −0.75 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 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: DIAMOND (Brandenburg & Putz, 2006 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006515/si2152sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006515/si2152Isup2.hkl

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

[Ni(C12H7N2O4)2]·4H2O	Z = 2
Mr = 617.17	F(000) = 636
Triclinic, P1	Dx = 1.659 Mg m−3
a = 9.990 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.896 (2) Å	Cell parameters from 3636 reflections
c = 12.565 (3) Å	θ = 1.8–27.9°
α = 112.97 (3)°	µ = 0.86 mm−1
β = 100.09 (3)°	T = 113 K
γ = 90.30 (3)°	Block, green
V = 1235.7 (4) Å3	0.20 × 0.10 × 0.08 mm

Rigaku Saturn CCD area-detector diffractometer	4305 independent reflections
Radiation source: rotating anode	2745 reflections with I > 2σ(I)
confocal	Rint = 0.126
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 1.8°
ω and φ scans	h = −10→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→11
Tmin = 0.846, Tmax = 0.934	l = −14→14
7165 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1025P)2] where P = (Fo2 + 2Fc2)/3
4305 reflections	(Δ/σ)max < 0.001
372 parameters	Δρmax = 0.96 e Å−3
0 restraints	Δρmin = −0.75 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	0.26176 (6)	0.23748 (6)	0.25373 (5)	0.0128 (3)
O1	0.1825 (4)	0.4096 (3)	0.3635 (3)	0.0170 (9)
O2	0.0298 (4)	0.5584 (4)	0.3582 (3)	0.0206 (9)
O3	0.5431 (4)	0.0527 (4)	0.2154 (4)	0.0236 (10)
H3	0.6006	0.0445	0.2692	0.035*
O4	0.4382 (5)	−0.1285 (5)	0.2149 (4)	0.0463 (15)
O5	0.1553 (4)	0.1112 (3)	0.3108 (3)	0.0168 (8)
O6	0.1883 (4)	0.0088 (4)	0.4363 (4)	0.0259 (10)
O7	0.3576 (4)	0.2726 (4)	−0.0101 (4)	0.0279 (10)
H7	0.3161	0.2681	−0.0759	0.042*
O8	0.2810 (5)	0.4775 (5)	0.0577 (5)	0.0513 (15)
N1	0.1132 (4)	0.2644 (4)	0.1406 (4)	0.0130 (10)
N2	0.2678 (4)	0.0647 (4)	0.0940 (4)	0.0113 (9)
N3	0.3979 (4)	0.2352 (4)	0.3886 (4)	0.0130 (10)
N4	0.4370 (4)	0.3585 (4)	0.2514 (4)	0.0142 (10)
C1	0.0871 (5)	0.4564 (5)	0.3123 (5)	0.0161 (12)
C2	0.0440 (5)	0.3747 (5)	0.1788 (5)	0.0149 (12)
C3	−0.0525 (5)	0.4060 (5)	0.1044 (5)	0.0194 (13)
H3A	−0.0980	0.4855	0.1320	0.023*
C4	−0.0825 (5)	0.3167 (5)	−0.0151 (5)	0.0192 (13)
H4	−0.1482	0.3361	−0.0696	0.023*
C5	−0.0156 (5)	0.2000 (5)	−0.0527 (5)	0.0179 (13)
H5	−0.0385	0.1370	−0.1321	0.021*
C6	0.0848 (5)	0.1768 (5)	0.0271 (4)	0.0110 (11)
C7	0.1705 (5)	0.0604 (5)	0.0014 (5)	0.0108 (11)
C8	0.1510 (5)	−0.0456 (5)	−0.1094 (5)	0.0134 (12)
H8	0.0834	−0.0443	−0.1723	0.016*
C9	0.2307 (5)	−0.1519 (5)	−0.1265 (5)	0.0217 (13)
H9	0.2192	−0.2246	−0.2012	0.026*
C10	0.3280 (5)	−0.1511 (5)	−0.0330 (5)	0.0188 (13)
H10	0.3835	−0.2237	−0.0422	0.023*
C11	0.3433 (5)	−0.0420 (5)	0.0749 (5)	0.0141 (12)
C12	0.4464 (5)	−0.0429 (5)	0.1771 (5)	0.0185 (13)
C13	0.2244 (6)	0.0881 (5)	0.3940 (5)	0.0188 (13)
C14	0.3639 (5)	0.1643 (5)	0.4469 (5)	0.0154 (12)
C15	0.4503 (5)	0.1663 (5)	0.5468 (5)	0.0177 (12)
H15	0.4258	0.1160	0.5885	0.021*
C16	0.5741 (5)	0.2441 (5)	0.5845 (5)	0.0172 (12)
H16	0.6354	0.2474	0.6527	0.021*
C17	0.6077 (5)	0.3174 (5)	0.5216 (5)	0.0162 (12)
H17	0.6919	0.3705	0.5461	0.019*
C18	0.5161 (5)	0.3109 (5)	0.4234 (5)	0.0139 (12)
C19	0.5397 (5)	0.3818 (5)	0.3460 (5)	0.0142 (12)
C20	0.6567 (5)	0.4637 (5)	0.3709 (5)	0.0175 (12)
H20	0.7262	0.4751	0.4369	0.021*
C21	0.6713 (6)	0.5292 (5)	0.2978 (5)	0.0211 (13)
H21	0.7510	0.5860	0.3130	0.025*
C22	0.5682 (6)	0.5107 (5)	0.2029 (5)	0.0215 (13)
H22	0.5741	0.5566	0.1531	0.026*
C23	0.4553 (5)	0.4231 (5)	0.1817 (5)	0.0166 (12)
C24	0.3523 (5)	0.3942 (5)	0.0712 (5)	0.0189 (12)
O9	0.7524 (3)	0.0424 (4)	0.3682 (3)	0.0213 (9)
H9A	0.8078	0.1092	0.3909	0.026*
H9B	0.7826	0.0158	0.4206	0.026*
O10	0.0754 (4)	0.7452 (4)	0.5945 (3)	0.0225 (9)
H10A	0.0597	0.6738	0.5353	0.027*
H10B	−0.0039	0.7536	0.6057	0.027*
O11	0.2191 (4)	0.2207 (4)	0.7879 (4)	0.0285 (10)
H11A	0.2309	0.1439	0.7435	0.034*
H11B	0.1365	0.2302	0.7714	0.034*
O12	0.0448 (4)	0.7657 (4)	0.2859 (4)	0.0331 (11)
H12A	0.0511	0.7113	0.3179	0.040*
H12B	0.0670	0.8384	0.3429	0.040*

	U11	U22	U33	U12	U13	U23
Ni1	0.0129 (4)	0.0140 (4)	0.0094 (4)	0.0003 (3)	−0.0015 (3)	0.0039 (3)
O1	0.0182 (19)	0.019 (2)	0.011 (2)	0.0034 (16)	0.0013 (16)	0.0030 (16)
O2	0.026 (2)	0.017 (2)	0.016 (2)	0.0074 (17)	0.0057 (18)	0.0026 (17)
O3	0.022 (2)	0.031 (2)	0.021 (2)	−0.0004 (18)	−0.0032 (18)	0.0160 (19)
O4	0.049 (3)	0.057 (3)	0.041 (3)	−0.021 (2)	−0.018 (3)	0.039 (3)
O5	0.0155 (18)	0.0175 (19)	0.017 (2)	−0.0024 (15)	−0.0002 (16)	0.0075 (16)
O6	0.026 (2)	0.028 (2)	0.025 (2)	−0.0090 (18)	−0.0022 (19)	0.016 (2)
O7	0.030 (2)	0.024 (2)	0.023 (2)	0.0009 (18)	−0.0092 (19)	0.0076 (19)
O8	0.056 (3)	0.030 (3)	0.047 (3)	0.015 (2)	−0.022 (3)	0.005 (2)
N1	0.012 (2)	0.016 (2)	0.012 (2)	−0.0013 (18)	0.0019 (18)	0.006 (2)
N2	0.011 (2)	0.015 (2)	0.008 (2)	0.0007 (17)	0.0021 (18)	0.0052 (18)
N3	0.016 (2)	0.014 (2)	0.009 (2)	0.0040 (18)	0.0026 (19)	0.0040 (18)
N4	0.013 (2)	0.010 (2)	0.016 (2)	0.0051 (17)	0.0036 (19)	0.0015 (19)
C1	0.019 (3)	0.013 (3)	0.013 (3)	0.000 (2)	0.001 (2)	0.003 (2)
C2	0.018 (3)	0.013 (3)	0.013 (3)	0.002 (2)	0.003 (2)	0.004 (2)
C3	0.015 (3)	0.021 (3)	0.021 (3)	0.004 (2)	0.003 (2)	0.008 (3)
C4	0.017 (3)	0.023 (3)	0.017 (3)	0.005 (2)	−0.001 (2)	0.010 (2)
C5	0.017 (3)	0.017 (3)	0.017 (3)	−0.004 (2)	−0.002 (2)	0.007 (2)
C6	0.015 (3)	0.011 (3)	0.007 (3)	−0.001 (2)	0.005 (2)	0.004 (2)
C7	0.010 (2)	0.011 (2)	0.012 (3)	0.001 (2)	0.004 (2)	0.004 (2)
C8	0.013 (3)	0.014 (3)	0.012 (3)	−0.001 (2)	0.002 (2)	0.004 (2)
C9	0.022 (3)	0.023 (3)	0.014 (3)	0.001 (2)	0.002 (3)	0.001 (2)
C10	0.021 (3)	0.018 (3)	0.016 (3)	0.006 (2)	0.002 (2)	0.005 (2)
C11	0.014 (3)	0.018 (3)	0.011 (3)	0.000 (2)	0.001 (2)	0.006 (2)
C12	0.018 (3)	0.017 (3)	0.018 (3)	0.002 (2)	0.001 (2)	0.006 (2)
C13	0.022 (3)	0.022 (3)	0.012 (3)	0.002 (2)	−0.002 (2)	0.008 (2)
C14	0.018 (3)	0.014 (3)	0.014 (3)	0.000 (2)	0.000 (2)	0.007 (2)
C15	0.020 (3)	0.018 (3)	0.015 (3)	0.003 (2)	0.003 (2)	0.007 (2)
C16	0.019 (3)	0.023 (3)	0.009 (3)	0.002 (2)	−0.002 (2)	0.007 (2)
C17	0.017 (3)	0.017 (3)	0.010 (3)	−0.001 (2)	−0.001 (2)	0.002 (2)
C18	0.013 (3)	0.011 (2)	0.015 (3)	0.002 (2)	0.000 (2)	0.004 (2)
C19	0.016 (3)	0.011 (3)	0.011 (3)	0.003 (2)	0.003 (2)	−0.001 (2)
C20	0.017 (3)	0.017 (3)	0.017 (3)	0.001 (2)	0.002 (2)	0.005 (2)
C21	0.021 (3)	0.026 (3)	0.016 (3)	0.000 (2)	0.004 (2)	0.008 (3)
C22	0.024 (3)	0.019 (3)	0.020 (3)	−0.001 (2)	0.007 (3)	0.006 (2)
C23	0.018 (3)	0.015 (3)	0.016 (3)	0.008 (2)	0.006 (2)	0.005 (2)
C24	0.018 (3)	0.022 (3)	0.020 (3)	0.004 (2)	0.005 (2)	0.011 (3)
O9	0.019 (2)	0.022 (2)	0.021 (2)	0.0013 (16)	−0.0014 (18)	0.0083 (18)
O10	0.0187 (19)	0.025 (2)	0.019 (2)	0.0007 (17)	0.0052 (18)	0.0025 (18)
O11	0.030 (2)	0.029 (2)	0.021 (2)	0.0026 (19)	−0.0017 (19)	0.0071 (19)
O12	0.042 (3)	0.027 (2)	0.028 (3)	−0.008 (2)	−0.003 (2)	0.013 (2)

Ni1—N1	1.975 (4)	C7—C8	1.399 (7)
Ni1—N3	1.987 (4)	C8—C9	1.377 (7)
Ni1—O1	2.104 (4)	C8—H8	0.9500
Ni1—O5	2.136 (4)	C9—C10	1.385 (7)
Ni1—N2	2.161 (5)	C9—H9	0.9500
Ni1—N4	2.197 (4)	C10—C11	1.394 (7)
O1—C1	1.276 (6)	C10—H10	0.9500
O2—C1	1.231 (6)	C11—C12	1.503 (6)
O3—C12	1.299 (6)	C13—C14	1.519 (7)
O3—H3	0.8400	C14—C15	1.385 (7)
O4—C12	1.207 (6)	C15—C16	1.394 (7)
O5—C13	1.260 (6)	C15—H15	0.9500
O6—C13	1.258 (6)	C16—C17	1.399 (7)
O7—C24	1.329 (7)	C16—H16	0.9500
O7—H7	0.8400	C17—C18	1.379 (7)
O8—C24	1.202 (6)	C17—H17	0.9500
N1—C6	1.348 (7)	C18—C19	1.505 (7)
N1—C2	1.352 (6)	C19—C20	1.379 (8)
N2—C11	1.354 (6)	C20—C21	1.390 (7)
N2—C7	1.364 (6)	C20—H20	0.9500
N3—C14	1.332 (7)	C21—C22	1.380 (7)
N3—C18	1.339 (6)	C21—H21	0.9500
N4—C23	1.354 (7)	C22—C23	1.392 (7)
N4—C19	1.365 (6)	C22—H22	0.9500
C1—C2	1.539 (7)	C23—C24	1.496 (7)
C2—C3	1.363 (6)	O9—H9A	0.8341
C3—C4	1.410 (8)	O9—H9B	0.8302
C3—H3A	0.9500	O10—H10A	0.8296
C4—C5	1.392 (7)	O10—H10B	0.8283
C4—H4	0.9500	O11—H11A	0.8278
C5—C6	1.387 (6)	O11—H11B	0.8319
C5—H5	0.9500	O12—H12A	0.8320
C6—C7	1.495 (7)	O12—H12B	0.8299
N1—Ni1—N3	170.11 (18)	C7—C8—H8	120.3
N1—Ni1—O1	78.57 (16)	C8—C9—C10	118.9 (5)
N3—Ni1—O1	91.64 (15)	C8—C9—H9	120.5
N1—Ni1—O5	100.61 (15)	C10—C9—H9	120.5
N3—Ni1—O5	78.13 (15)	C9—C10—C11	118.9 (5)
O1—Ni1—O5	92.18 (14)	C9—C10—H10	120.5
N1—Ni1—N2	78.15 (17)	C11—C10—H10	120.5
N3—Ni1—N2	111.50 (16)	N2—C11—C10	123.5 (4)
O1—Ni1—N2	156.37 (14)	N2—C11—C12	117.6 (5)
O5—Ni1—N2	88.21 (15)	C10—C11—C12	118.8 (4)
N1—Ni1—N4	103.32 (16)	O4—C12—O3	125.4 (5)
N3—Ni1—N4	78.03 (17)	O4—C12—C11	121.3 (5)
O1—Ni1—N4	91.03 (15)	O3—C12—C11	113.3 (4)
O5—Ni1—N4	156.02 (15)	O6—C13—O5	126.1 (5)
N2—Ni1—N4	98.14 (17)	O6—C13—C14	117.9 (4)
C1—O1—Ni1	115.9 (3)	O5—C13—C14	116.0 (5)
C12—O3—H3	109.5	N3—C14—C15	120.9 (5)
C13—O5—Ni1	114.2 (3)	N3—C14—C13	113.2 (4)
C24—O7—H7	109.5	C15—C14—C13	125.8 (5)
C6—N1—C2	121.0 (4)	C14—C15—C16	118.3 (5)
C6—N1—Ni1	120.6 (3)	C14—C15—H15	120.9
C2—N1—Ni1	118.4 (3)	C16—C15—H15	120.9
C11—N2—C7	116.5 (5)	C15—C16—C17	119.7 (5)
C11—N2—Ni1	130.6 (3)	C15—C16—H16	120.1
C7—N2—Ni1	112.6 (3)	C17—C16—H16	120.1
C14—N3—C18	121.8 (4)	C18—C17—C16	118.6 (5)
C14—N3—Ni1	118.1 (3)	C18—C17—H17	120.7
C18—N3—Ni1	119.9 (3)	C16—C17—H17	120.7
C23—N4—C19	115.6 (4)	N3—C18—C17	120.6 (5)
C23—N4—Ni1	132.1 (3)	N3—C18—C19	114.9 (4)
C19—N4—Ni1	111.9 (3)	C17—C18—C19	124.5 (5)
O2—C1—O1	127.0 (5)	N4—C19—C20	123.8 (5)
O2—C1—C2	118.6 (4)	N4—C19—C18	114.7 (4)
O1—C1—C2	114.4 (5)	C20—C19—C18	121.5 (4)
N1—C2—C3	122.0 (5)	C19—C20—C21	118.9 (5)
N1—C2—C1	112.4 (4)	C19—C20—H20	120.6
C3—C2—C1	125.6 (5)	C21—C20—H20	120.6
C2—C3—C4	117.9 (5)	C22—C21—C20	119.0 (5)
C2—C3—H3A	121.1	C22—C21—H21	120.5
C4—C3—H3A	121.1	C20—C21—H21	120.5
C5—C4—C3	119.8 (5)	C21—C22—C23	118.5 (5)
C5—C4—H4	120.1	C21—C22—H22	120.7
C3—C4—H4	120.1	C23—C22—H22	120.7
C6—C5—C4	119.2 (5)	N4—C23—C22	124.1 (5)
C6—C5—H5	120.4	N4—C23—C24	118.6 (5)
C4—C5—H5	120.4	C22—C23—C24	117.2 (5)
N1—C6—C5	120.0 (5)	O8—C24—O7	125.3 (5)
N1—C6—C7	113.5 (4)	O8—C24—C23	122.1 (5)
C5—C6—C7	126.5 (5)	O7—C24—C23	112.4 (4)
N2—C7—C8	122.7 (4)	H9A—O9—H9B	97.5
N2—C7—C6	115.1 (4)	H10A—O10—H10B	97.1
C8—C7—C6	122.2 (4)	H11A—O11—H11B	106.3
C9—C8—C7	119.4 (5)	H12A—O12—H12B	102.5
C9—C8—H8	120.3
N1—Ni1—O1—C1	−3.7 (4)	Ni1—N1—C6—C7	2.8 (6)
N3—Ni1—O1—C1	177.7 (4)	C4—C5—C6—N1	2.4 (8)
O5—Ni1—O1—C1	−104.1 (4)	C4—C5—C6—C7	−177.5 (5)
N2—Ni1—O1—C1	−13.6 (6)	C11—N2—C7—C8	−2.2 (7)
N4—Ni1—O1—C1	99.7 (4)	Ni1—N2—C7—C8	−176.9 (4)
N1—Ni1—O5—C13	−173.4 (4)	C11—N2—C7—C6	177.3 (4)
N3—Ni1—O5—C13	−3.4 (4)	Ni1—N2—C7—C6	2.6 (5)
O1—Ni1—O5—C13	−94.6 (4)	N1—C6—C7—N2	−3.5 (6)
N2—Ni1—O5—C13	109.0 (4)	C5—C6—C7—N2	176.4 (5)
N4—Ni1—O5—C13	2.8 (6)	N1—C6—C7—C8	176.0 (4)
N3—Ni1—N1—C6	−168.7 (8)	C5—C6—C7—C8	−4.1 (8)
O1—Ni1—N1—C6	−177.2 (4)	N2—C7—C8—C9	1.3 (8)
O5—Ni1—N1—C6	−87.1 (4)	C6—C7—C8—C9	−178.1 (5)
N2—Ni1—N1—C6	−1.2 (4)	C7—C8—C9—C10	0.2 (8)
N4—Ni1—N1—C6	94.5 (4)	C8—C9—C10—C11	−0.8 (8)
N3—Ni1—N1—C2	13.4 (12)	C7—N2—C11—C10	1.5 (7)
O1—Ni1—N1—C2	5.0 (4)	Ni1—N2—C11—C10	175.2 (4)
O5—Ni1—N1—C2	95.1 (4)	C7—N2—C11—C12	−177.0 (4)
N2—Ni1—N1—C2	−179.0 (4)	Ni1—N2—C11—C12	−3.3 (7)
N4—Ni1—N1—C2	−83.3 (4)	C9—C10—C11—N2	−0.1 (8)
N1—Ni1—N2—C11	−174.7 (5)	C9—C10—C11—C12	178.4 (5)
N3—Ni1—N2—C11	3.0 (5)	N2—C11—C12—O4	117.9 (6)
O1—Ni1—N2—C11	−164.9 (4)	C10—C11—C12—O4	−60.7 (8)
O5—Ni1—N2—C11	−73.5 (4)	N2—C11—C12—O3	−64.1 (7)
N4—Ni1—N2—C11	83.3 (4)	C10—C11—C12—O3	117.3 (6)
N1—Ni1—N2—C7	−0.9 (3)	Ni1—O5—C13—O6	−174.0 (5)
N3—Ni1—N2—C7	176.8 (3)	Ni1—O5—C13—C14	6.1 (6)
O1—Ni1—N2—C7	9.0 (6)	C18—N3—C14—C15	0.1 (8)
O5—Ni1—N2—C7	100.3 (3)	Ni1—N3—C14—C15	−175.3 (4)
N4—Ni1—N2—C7	−102.9 (3)	C18—N3—C14—C13	178.8 (5)
N1—Ni1—N3—C14	83.3 (10)	Ni1—N3—C14—C13	3.3 (6)
O1—Ni1—N3—C14	91.6 (4)	O6—C13—C14—N3	173.7 (5)
O5—Ni1—N3—C14	−0.3 (4)	O5—C13—C14—N3	−6.4 (7)
N2—Ni1—N3—C14	−83.6 (4)	O6—C13—C14—C15	−7.7 (9)
N4—Ni1—N3—C14	−177.7 (4)	O5—C13—C14—C15	172.2 (5)
N1—Ni1—N3—C18	−92.2 (10)	N3—C14—C15—C16	−0.3 (8)
O1—Ni1—N3—C18	−84.0 (4)	C13—C14—C15—C16	−178.8 (5)
O5—Ni1—N3—C18	−175.9 (4)	C14—C15—C16—C17	0.1 (8)
N2—Ni1—N3—C18	100.9 (4)	C15—C16—C17—C18	0.3 (8)
N4—Ni1—N3—C18	6.7 (4)	C14—N3—C18—C17	0.3 (8)
N1—Ni1—N4—C23	−8.8 (5)	Ni1—N3—C18—C17	175.6 (4)
N3—Ni1—N4—C23	−178.8 (5)	C14—N3—C18—C19	178.7 (5)
O1—Ni1—N4—C23	−87.3 (5)	Ni1—N3—C18—C19	−6.0 (6)
O5—Ni1—N4—C23	175.0 (4)	C16—C17—C18—N3	−0.4 (8)
N2—Ni1—N4—C23	70.9 (5)	C16—C17—C18—C19	−178.7 (5)
N1—Ni1—N4—C19	163.7 (3)	C23—N4—C19—C20	−0.9 (8)
N3—Ni1—N4—C19	−6.3 (3)	Ni1—N4—C19—C20	−174.7 (4)
O1—Ni1—N4—C19	85.2 (3)	C23—N4—C19—C18	179.0 (4)
O5—Ni1—N4—C19	−12.5 (6)	Ni1—N4—C19—C18	5.2 (5)
N2—Ni1—N4—C19	−116.7 (3)	N3—C18—C19—N4	−0.1 (7)
Ni1—O1—C1—O2	−177.0 (5)	C17—C18—C19—N4	178.2 (5)
Ni1—O1—C1—C2	1.9 (6)	N3—C18—C19—C20	179.8 (5)
C6—N1—C2—C3	−3.1 (8)	C17—C18—C19—C20	−1.9 (8)
Ni1—N1—C2—C3	174.7 (4)	N4—C19—C20—C21	1.5 (8)
C6—N1—C2—C1	176.8 (4)	C18—C19—C20—C21	−178.4 (5)
Ni1—N1—C2—C1	−5.4 (6)	C19—C20—C21—C22	0.2 (8)
O2—C1—C2—N1	−178.9 (5)	C20—C21—C22—C23	−2.2 (8)
O1—C1—C2—N1	2.1 (7)	C19—N4—C23—C22	−1.3 (8)
O2—C1—C2—C3	1.0 (8)	Ni1—N4—C23—C22	170.9 (4)
O1—C1—C2—C3	−178.1 (5)	C19—N4—C23—C24	175.3 (4)
N1—C2—C3—C4	2.2 (8)	Ni1—N4—C23—C24	−12.4 (7)
C1—C2—C3—C4	−177.7 (5)	C21—C22—C23—N4	2.9 (9)
C2—C3—C4—C5	1.0 (8)	C21—C22—C23—C24	−173.8 (5)
C3—C4—C5—C6	−3.2 (8)	N4—C23—C24—O8	114.4 (7)
C2—N1—C6—C5	0.7 (7)	C22—C23—C24—O8	−68.8 (8)
Ni1—N1—C6—C5	−177.1 (4)	N4—C23—C24—O7	−70.5 (7)
C2—N1—C6—C7	−179.4 (4)	C22—C23—C24—O7	106.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12B···O6i	0.83	2.02	2.783 (6)	153
O12—H12A···O2	0.83	1.94	2.755 (5)	165
O11—H11B···O12ii	0.83	1.84	2.662 (5)	172
O11—H11A···O9iii	0.83	1.99	2.821 (6)	177
O10—H10B···O5ii	0.83	2.22	2.953 (5)	148
O10—H10A···O2	0.83	2.05	2.822 (6)	155
O9—H9B···O6iii	0.83	1.89	2.694 (5)	162
O9—H9A···O10iv	0.83	1.90	2.714 (5)	167
O7—H7···O11v	0.84	1.69	2.513 (5)	166
O3—H3···O9	0.84	1.79	2.614 (5)	166

Ni1—N1	1.975 (4)
Ni1—N3	1.987 (4)
Ni1—O1	2.104 (4)
Ni1—O5	2.136 (4)
Ni1—N2	2.161 (5)
Ni1—N4	2.197 (4)

N3—Ni1—N2	111.50 (16)
N1—Ni1—N4	103.32 (16)
N3—Ni1—N4	78.03 (17)
O5—Ni1—N4	156.02 (15)

N1—C6—C7—N2	−3.5 (6)
N3—C18—C19—N4	−0.1 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O12—H12B⋯O6i	0.83	2.02	2.783 (6)	153
O12—H12A⋯O2	0.83	1.94	2.755 (5)	165
O11—H11B⋯O12ii	0.83	1.84	2.662 (5)	172
O11—H11A⋯O9iii	0.83	1.99	2.821 (6)	177
O10—H10B⋯O5ii	0.83	2.22	2.953 (5)	148
O10—H10A⋯O2	0.83	2.05	2.822 (6)	155
O9—H9B⋯O6iii	0.83	1.89	2.694 (5)	162
O9—H9A⋯O10iv	0.83	1.90	2.714 (5)	167
O7—H7⋯O11v	0.84	1.69	2.513 (5)	166
O3—H3⋯O9	0.84	1.79	2.614 (5)	166

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