Hexakis(1H-imidazole-κN)nickel(II) triaqua-tris(1H-imidazole-κN)nickel(II) bis-(naphthalene-1,4-dicarboxyl-ate).

The crystal structure of the title compound, [Ni(C(3)H(4)N(2))(6)][Ni(C(3)H(4)N(2))(3)(H(2)O)(3)](C(12)H(6)O(4))(2), contains uncoordinated naphthalene-dicarboxyl-ate dianions and two kinds of Ni(II) complex cations, both assuming distorted octa-hedral geometries. One Ni(II) ion is located on an inversion center and is coordinated by six imidazole mol-ecules, while the other Ni(II) ion is located on a twofold rotation axis and is coordinated by three water mol-ecules and three imidazole mol-ecules in a mer-NiN(3)O(3) arrangement. The naphthalene-dicarboxyl-ate dianion links both Ni(II) complex cations via O-H⋯O and N-H⋯O hydrogen bonding, but no π-π stacking is observed between aromatic rings in the crystal structure. One imidazole ligand is equally disordered over two sites about a twofold rotation axis; one N atom and one water O atom have site symmetry 2.

Related literature

For general background, see: Su & Xu (2004 ▶); Xu et al. (2007 ▶). For related structures, see: Derissen et al. (1979 ▶); Li et al. (2008 ▶).

Experimental

Crystal data

[Ni(C3H4N2)6][Ni(C3H4N2)3(H2O)3](C12H6O4)2

M = 1212.54

Orthorhombic,

a = 29.301 (7) Å

b = 9.297 (2) Å

c = 20.381 (5) Å

V = 5552 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.75 mm−1

T = 294 (2) K

0.22 × 0.15 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.866, T max = 0.925

33285 measured reflections

4984 independent reflections

2653 reflections with I > 2σ(I)

R int = 0.128

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.140

S = 1.01

4984 reflections

367 parameters

5 restraints

H-atom parameters constrained

Δρmax = 0.95 e Å−3

Δρmin = −0.47 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024215/hb2767sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024215/hb2767Isup2.hkl

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

[Ni(C3H4N2)6][Ni(C3H4N2)3(H2O)3](C12H6O4)2	F000 = 2520
Mr = 1212.54	Dx = 1.451 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 5668 reflections
a = 29.301 (7) Å	θ = 2.2–24.5º
b = 9.297 (2) Å	µ = 0.75 mm−1
c = 20.381 (5) Å	T = 294 (2) K
V = 5552 (2) Å3	Prism, green
Z = 4	0.22 × 0.15 × 0.10 mm

Rigaku R-AXIS RAPID IP diffractometer	4984 independent reflections
Radiation source: fine-focus sealed tube	2653 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.128
Detector resolution: 10.0 pixels mm-1	θmax = 25.2º
T = 294(2) K	θmin = 1.4º
ω scans	h = −34→34
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	k = −9→11
Tmin = 0.866, Tmax = 0.925	l = −24→23
33285 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0559P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
4984 reflections	Δρmax = 0.95 e Å−3
367 parameters	Δρmin = −0.47 e Å−3
5 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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)
Ni1	0.5000	0.0000	0.5000	0.0358 (2)
Ni2	0.7500	0.7500	0.54570 (4)	0.0380 (2)
N1	0.53093 (12)	0.2040 (4)	0.50465 (18)	0.0392 (9)
N2	0.58307 (14)	0.3703 (4)	0.4922 (2)	0.0586 (12)
H2N	0.6058	0.4167	0.4759	0.070*
N3	0.54557 (13)	−0.0704 (4)	0.57414 (17)	0.0417 (10)
N4	0.58361 (13)	−0.2193 (4)	0.63876 (19)	0.0505 (11)
H4N	0.5921	−0.2980	0.6573	0.061*
N5	0.45162 (13)	0.0630 (4)	0.57239 (18)	0.0399 (9)
N6	0.41513 (15)	0.0694 (4)	0.6666 (2)	0.0570 (12)
H6N	0.4091	0.0576	0.7075	0.068*
N7	0.72172 (12)	0.9585 (4)	0.54389 (19)	0.0449 (10)
N8	0.69577 (14)	1.1727 (4)	0.5723 (2)	0.0612 (12)
H8N	0.6878	1.2441	0.5966	0.073*
O1	0.65246 (12)	0.5137 (4)	0.43190 (15)	0.0622 (10)
O2	0.69666 (14)	0.6205 (4)	0.36079 (17)	0.0887 (14)
O3	0.65981 (12)	0.0720 (3)	0.13293 (16)	0.0598 (10)
O4	0.60816 (11)	−0.0274 (3)	0.19982 (15)	0.0556 (9)
O1W	0.68332 (10)	0.6562 (3)	0.54323 (13)	0.0447 (8)
H1A	0.6741	0.6217	0.5028	0.067*
H1B	0.6780	0.5935	0.5724	0.067*
O2W	0.7500	0.7500	0.44632 (18)	0.0498 (12)
H2A	0.7342	0.6989	0.4207	0.075*
C1	0.56657 (18)	0.2458 (6)	0.4712 (2)	0.0546 (14)
H1	0.5790	0.1939	0.4365	0.066*
C2	0.5574 (2)	0.4100 (6)	0.5438 (3)	0.0690 (17)
H2	0.5610	0.4913	0.5698	0.083*
C3	0.52539 (18)	0.3080 (5)	0.5499 (3)	0.0598 (15)
H3	0.5023	0.3089	0.5812	0.072*
C4	0.54989 (17)	−0.2028 (5)	0.5955 (2)	0.0494 (13)
H4	0.5312	−0.2780	0.5818	0.059*
C5	0.60167 (18)	−0.0877 (6)	0.6475 (3)	0.0652 (16)
H5	0.6256	−0.0637	0.6755	0.078*
C6	0.57841 (17)	0.0030 (5)	0.6078 (2)	0.0547 (14)
H6	0.5840	0.1011	0.6040	0.066*
C7	0.45366 (17)	0.0319 (5)	0.6357 (2)	0.0501 (13)
H7	0.4786	−0.0106	0.6561	0.060*
C8	0.38765 (19)	0.1290 (6)	0.6211 (3)	0.0700 (17)
H8	0.3587	0.1667	0.6282	0.084*
C9	0.40963 (19)	0.1237 (6)	0.5646 (3)	0.0635 (15)
H9	0.3980	0.1568	0.5248	0.076*
C10	0.71259 (18)	1.0466 (5)	0.5928 (3)	0.0603 (15)
H10	0.7173	1.0236	0.6367	0.072*
C11	0.6937 (2)	1.1662 (6)	0.5064 (3)	0.0779 (18)
H11	0.6832	1.2378	0.4783	0.093*
C12	0.7098 (2)	1.0357 (6)	0.4888 (3)	0.0743 (18)
H12	0.7124	1.0028	0.4459	0.089*
C20	0.65761 (16)	0.4155 (5)	0.3246 (2)	0.0409 (12)
C21	0.69215 (17)	0.3443 (5)	0.2948 (2)	0.0571 (14)
H21	0.7221	0.3675	0.3057	0.069*
C22	0.68420 (16)	0.2359 (5)	0.2477 (2)	0.0541 (14)
H22	0.7090	0.1911	0.2278	0.065*
C23	0.64133 (15)	0.1953 (5)	0.2307 (2)	0.0395 (11)
C24	0.60336 (14)	0.2706 (5)	0.25953 (19)	0.0360 (11)
C25	0.55749 (15)	0.2431 (5)	0.2410 (2)	0.0443 (12)
H25	0.5514	0.1709	0.2107	0.053*
C26	0.52247 (17)	0.3195 (5)	0.2666 (2)	0.0511 (13)
H26	0.4927	0.2974	0.2544	0.061*
C27	0.53041 (17)	0.4317 (5)	0.3111 (2)	0.0525 (14)
H27	0.5061	0.4849	0.3276	0.063*
C28	0.57430 (17)	0.4625 (5)	0.3302 (2)	0.0493 (13)
H28	0.5794	0.5366	0.3599	0.059*
C29	0.61186 (15)	0.3837 (4)	0.3056 (2)	0.0376 (11)
C30	0.66958 (17)	0.5248 (5)	0.3766 (2)	0.0478 (13)
C31	0.63586 (17)	0.0716 (5)	0.1832 (2)	0.0447 (12)
N9	0.7500	0.7500	0.6462 (3)	0.0595 (12)
N10	0.7702 (3)	0.7153 (9)	0.7485 (3)	0.0595 (12)	0.50
H10A	0.7872	0.7128	0.7829	0.071*	0.50
C13	0.7844 (2)	0.7501 (13)	0.6881 (3)	0.0595 (12)	0.50
H13	0.8144	0.7715	0.6771	0.071*	0.50
C14	0.7248 (3)	0.6846 (11)	0.7474 (4)	0.0595 (12)	0.50
H14	0.7062	0.6550	0.7818	0.071*	0.50
C15	0.7135 (2)	0.7078 (13)	0.6836 (4)	0.0595 (12)	0.50
H15	0.6841	0.6963	0.6671	0.071*	0.50

	U11	U22	U33	U12	U13	U23
Ni1	0.0416 (5)	0.0306 (5)	0.0353 (4)	0.0021 (4)	0.0028 (4)	0.0023 (4)
Ni2	0.0463 (5)	0.0360 (5)	0.0316 (5)	−0.0068 (4)	0.000	0.000
N1	0.042 (2)	0.033 (2)	0.043 (2)	−0.0010 (18)	−0.002 (2)	0.0025 (19)
N2	0.065 (3)	0.048 (3)	0.063 (3)	−0.020 (2)	0.006 (2)	0.006 (2)
N3	0.052 (3)	0.031 (2)	0.042 (2)	0.001 (2)	0.001 (2)	0.0034 (19)
N4	0.053 (3)	0.046 (3)	0.052 (3)	0.010 (2)	−0.007 (2)	0.012 (2)
N5	0.045 (3)	0.033 (2)	0.041 (2)	−0.0024 (19)	0.0020 (19)	0.0027 (18)
N6	0.063 (3)	0.064 (3)	0.044 (3)	−0.002 (2)	0.016 (2)	−0.004 (2)
N7	0.048 (2)	0.040 (2)	0.046 (3)	−0.0051 (19)	−0.002 (2)	0.001 (2)
N8	0.062 (3)	0.039 (3)	0.082 (4)	0.001 (2)	0.006 (3)	−0.002 (3)
O1	0.084 (3)	0.066 (3)	0.0359 (19)	−0.031 (2)	0.0086 (19)	−0.0142 (18)
O2	0.118 (3)	0.101 (3)	0.047 (2)	−0.069 (3)	0.004 (2)	−0.013 (2)
O3	0.084 (3)	0.052 (2)	0.043 (2)	−0.0058 (19)	0.022 (2)	−0.0143 (17)
O4	0.070 (2)	0.045 (2)	0.052 (2)	−0.0141 (18)	0.0050 (18)	−0.0095 (17)
O1W	0.053 (2)	0.047 (2)	0.0348 (18)	−0.0090 (15)	0.0016 (15)	0.0027 (15)
O2W	0.068 (3)	0.054 (3)	0.028 (2)	−0.027 (2)	0.000	0.000
C1	0.069 (4)	0.046 (3)	0.048 (3)	−0.013 (3)	0.009 (3)	−0.010 (3)
C2	0.083 (4)	0.043 (3)	0.081 (5)	−0.013 (3)	0.004 (4)	−0.018 (3)
C3	0.059 (4)	0.041 (3)	0.080 (4)	0.000 (3)	0.015 (3)	−0.011 (3)
C4	0.053 (3)	0.043 (3)	0.053 (3)	0.003 (2)	−0.007 (3)	0.007 (3)
C5	0.069 (4)	0.051 (4)	0.076 (4)	0.004 (3)	−0.032 (3)	0.001 (3)
C6	0.060 (3)	0.032 (3)	0.073 (4)	−0.003 (3)	−0.019 (3)	0.004 (3)
C7	0.054 (3)	0.057 (3)	0.039 (3)	0.001 (3)	0.004 (3)	−0.007 (3)
C8	0.059 (4)	0.084 (5)	0.067 (4)	0.028 (3)	0.022 (3)	−0.003 (3)
C9	0.062 (4)	0.070 (4)	0.058 (4)	0.018 (3)	0.003 (3)	0.010 (3)
C10	0.085 (4)	0.039 (3)	0.057 (4)	0.000 (3)	0.005 (3)	0.007 (3)
C11	0.093 (5)	0.064 (4)	0.077 (5)	0.026 (3)	−0.008 (4)	0.013 (4)
C12	0.106 (5)	0.057 (4)	0.060 (4)	0.029 (3)	−0.012 (3)	0.007 (3)
C20	0.049 (3)	0.038 (3)	0.037 (3)	−0.007 (2)	0.000 (2)	−0.007 (2)
C21	0.043 (3)	0.070 (4)	0.058 (3)	−0.015 (3)	−0.003 (3)	−0.023 (3)
C22	0.041 (3)	0.062 (4)	0.059 (3)	−0.002 (3)	0.008 (3)	−0.018 (3)
C23	0.040 (3)	0.046 (3)	0.033 (3)	−0.005 (2)	0.001 (2)	−0.007 (2)
C24	0.038 (3)	0.041 (3)	0.029 (2)	−0.001 (2)	−0.001 (2)	−0.001 (2)
C25	0.044 (3)	0.048 (3)	0.041 (3)	−0.003 (3)	−0.007 (2)	−0.004 (2)
C26	0.042 (3)	0.060 (3)	0.052 (3)	−0.001 (3)	−0.004 (3)	0.003 (3)
C27	0.048 (3)	0.050 (3)	0.059 (4)	0.019 (3)	−0.003 (3)	−0.003 (3)
C28	0.057 (3)	0.048 (3)	0.043 (3)	0.004 (3)	0.001 (3)	−0.002 (2)
C29	0.043 (3)	0.034 (3)	0.036 (3)	0.001 (2)	−0.002 (2)	0.000 (2)
C30	0.056 (3)	0.048 (3)	0.040 (3)	−0.013 (3)	0.000 (3)	−0.008 (2)
C31	0.057 (3)	0.037 (3)	0.040 (3)	0.001 (3)	−0.011 (3)	−0.010 (2)
N9	0.078 (3)	0.062 (3)	0.039 (2)	0.005 (3)	0.000	0.000
N10	0.078 (3)	0.062 (3)	0.039 (2)	0.005 (3)	0.000	0.000
C13	0.078 (3)	0.062 (3)	0.039 (2)	0.005 (3)	0.000	0.000
C14	0.078 (3)	0.062 (3)	0.039 (2)	0.005 (3)	0.000	0.000
C15	0.078 (3)	0.062 (3)	0.039 (2)	0.005 (3)	0.000	0.000

Ni1—N1	2.104 (3)	C4—H4	0.9300
Ni1—N1i	2.104 (3)	C5—C6	1.353 (6)
Ni1—N3	2.120 (4)	C5—H5	0.9300
Ni1—N3i	2.120 (4)	C6—H6	0.9300
Ni1—N5	2.128 (4)	C7—H7	0.9300
Ni1—N5i	2.128 (4)	C8—C9	1.321 (6)
Ni2—O1Wii	2.140 (3)	C8—H8	0.9300
Ni2—O1W	2.140 (3)	C9—H9	0.9300
Ni2—O2W	2.025 (4)	C10—H10	0.9300
Ni2—N7ii	2.108 (4)	C11—C12	1.349 (7)
Ni2—N7	2.108 (4)	C11—H11	0.9300
Ni2—N9ii	2.048 (5)	C12—H12	0.9300
Ni2—N9	2.048 (5)	C20—C21	1.353 (6)
N1—C1	1.306 (5)	C20—C29	1.426 (6)
N1—C3	1.346 (6)	C20—C30	1.510 (6)
N2—C1	1.325 (6)	C21—C22	1.411 (6)
N2—C2	1.345 (6)	C21—H21	0.9300
N2—H2N	0.8600	C22—C23	1.357 (6)
N3—C4	1.312 (5)	C22—H22	0.9300
N3—C6	1.365 (5)	C23—C24	1.440 (6)
N4—C4	1.333 (5)	C23—C31	1.511 (6)
N4—C5	1.344 (6)	C24—C25	1.419 (6)
N4—H4N	0.8600	C24—C29	1.432 (5)
N5—C7	1.323 (5)	C25—C26	1.352 (6)
N5—C9	1.363 (6)	C25—H25	0.9300
N6—C7	1.339 (5)	C26—C27	1.402 (6)
N6—C8	1.347 (6)	C26—H26	0.9300
N6—H6N	0.8600	C27—C28	1.374 (6)
N7—C10	1.317 (6)	C27—H27	0.9300
N7—C12	1.377 (6)	C28—C29	1.414 (6)
N8—C10	1.338 (6)	C28—H28	0.9300
N8—C11	1.347 (6)	N9—N9ii	0.000 (10)
N8—H8N	0.8600	N9—C13	1.3201 (11)
O1—C30	1.238 (5)	N9—C13ii	1.3201 (11)
O2—C30	1.235 (5)	N9—C15ii	1.3703 (11)
O3—C31	1.243 (5)	N9—C15	1.3703 (11)
O4—C31	1.272 (5)	N10—C13	1.3399 (11)
O1W—H1A	0.9247	N10—C14	1.3603 (11)
O1W—H1B	0.8470	N10—H10A	0.8600
O2W—H2A	0.8443	C13—H13	0.9300
C1—H1	0.9300	C14—C15	1.3599 (11)
C2—C3	1.338 (7)	C14—C14ii	1.912 (16)
C2—H2	0.9300	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
N1—Ni1—N1i	180.0	C5—C6—H6	124.9
N1—Ni1—N3	88.56 (14)	N3—C6—H6	124.9
N1i—Ni1—N3	91.44 (14)	N5—C7—N6	111.3 (4)
N1—Ni1—N3i	91.44 (14)	N5—C7—H7	124.3
N1i—Ni1—N3i	88.56 (14)	N6—C7—H7	124.3
N3—Ni1—N3i	180.0	C9—C8—N6	107.1 (5)
N1—Ni1—N5	90.44 (14)	C9—C8—H8	126.5
N1i—Ni1—N5	89.56 (14)	N6—C8—H8	126.5
N3—Ni1—N5	90.59 (14)	C8—C9—N5	110.7 (5)
N3i—Ni1—N5	89.41 (14)	C8—C9—H9	124.7
N1—Ni1—N5i	89.56 (14)	N5—C9—H9	124.7
N1i—Ni1—N5i	90.44 (14)	N7—C10—N8	112.6 (5)
N3—Ni1—N5i	89.41 (14)	N7—C10—H10	123.7
N3i—Ni1—N5i	90.59 (14)	N8—C10—H10	123.7
N5—Ni1—N5i	180.0	N8—C11—C12	106.8 (5)
O2W—Ni2—N9	180.0	N8—C11—H11	126.6
O2W—Ni2—N7ii	89.00 (11)	C12—C11—H11	126.6
N9ii—Ni2—N7ii	91.00 (11)	C11—C12—N7	109.9 (5)
O2W—Ni2—N7	89.00 (11)	C11—C12—H12	125.0
N9—Ni2—N7	91.00 (11)	N7—C12—H12	125.0
N7ii—Ni2—N7	178.0 (2)	C21—C20—C29	118.7 (4)
O2W—Ni2—O1Wii	88.65 (8)	C21—C20—C30	118.1 (4)
N9—Ni2—O1Wii	91.35 (8)	C29—C20—C30	123.2 (4)
N7ii—Ni2—O1Wii	90.87 (12)	C20—C21—C22	122.1 (4)
N7—Ni2—O1Wii	89.08 (12)	C20—C21—H21	119.0
O2W—Ni2—O1W	88.65 (8)	C22—C21—H21	119.0
N9—Ni2—O1W	91.35 (8)	C23—C22—C21	121.7 (4)
N7ii—Ni2—O1W	89.08 (12)	C23—C22—H22	119.2
N7—Ni2—O1W	90.87 (12)	C21—C22—H22	119.2
O1Wii—Ni2—O1W	177.31 (15)	C22—C23—C24	118.4 (4)
C1—N1—C3	103.9 (4)	C22—C23—C31	118.3 (4)
C1—N1—Ni1	126.1 (3)	C24—C23—C31	123.3 (4)
C3—N1—Ni1	128.8 (3)	C25—C24—C29	118.1 (4)
C1—N2—C2	106.7 (4)	C25—C24—C23	122.4 (4)
C1—N2—H2N	126.7	C29—C24—C23	119.4 (4)
C2—N2—H2N	126.7	C26—C25—C24	121.5 (4)
C4—N3—C6	103.5 (4)	C26—C25—H25	119.3
C4—N3—Ni1	126.0 (3)	C24—C25—H25	119.3
C6—N3—Ni1	130.4 (3)	C25—C26—C27	120.9 (5)
C4—N4—C5	106.0 (4)	C25—C26—H26	119.5
C4—N4—H4N	127.0	C27—C26—H26	119.5
C5—N4—H4N	127.0	C28—C27—C26	119.6 (5)
C7—N5—C9	104.2 (4)	C28—C27—H27	120.2
C7—N5—Ni1	125.8 (3)	C26—C27—H27	120.2
C9—N5—Ni1	129.3 (3)	C27—C28—C29	121.4 (4)
C7—N6—C8	106.7 (4)	C27—C28—H28	119.3
C7—N6—H6N	126.6	C29—C28—H28	119.3
C8—N6—H6N	126.6	C28—C29—C20	121.9 (4)
C10—N7—C12	103.9 (4)	C28—C29—C24	118.5 (4)
C10—N7—Ni2	129.7 (3)	C20—C29—C24	119.5 (4)
C12—N7—Ni2	126.4 (3)	O2—C30—O1	123.9 (4)
C10—N8—C11	106.7 (5)	O2—C30—C20	116.8 (4)
C10—N8—H8N	126.6	O1—C30—C20	119.3 (4)
C11—N8—H8N	126.6	O3—C31—O4	125.6 (4)
Ni2—O1W—H1A	115.3	O3—C31—C23	117.7 (4)
Ni2—O1W—H1B	115.5	O4—C31—C23	116.6 (4)
H1A—O1W—H1B	109.4	C13—N9—C15	103.6 (6)
Ni2—O2W—H2A	128.2	C13—N9—Ni2	130.3 (4)
N1—C1—N2	112.6 (4)	C15—N9—Ni2	123.8 (4)
N1—C1—H1	123.7	C13—N10—C14	109.8 (8)
N2—C1—H1	123.7	C13—N10—H10A	125.1
C3—C2—N2	105.7 (5)	C14—N10—H10A	125.1
C3—C2—H2	127.2	N9—C13—N10	111.0 (7)
N2—C2—H2	127.2	N9—C13—H13	124.5
C2—C3—N1	111.2 (5)	N10—C13—H13	124.5
C2—C3—H3	124.4	C15—C14—N10	102.8 (8)
N1—C3—H3	124.4	C15—C14—C14ii	95.0 (5)
N3—C4—N4	113.5 (4)	C15—C14—H14	128.6
N3—C4—H4	123.2	N10—C14—H14	128.6
N4—C4—H4	123.2	C14ii—C14—H14	129.9
N4—C5—C6	106.8 (5)	C14—C15—N9	112.8 (7)
N4—C5—H5	126.6	C14—C15—H15	123.6
C6—C5—H5	126.6	N9—C15—H15	123.6
C5—C6—N3	110.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O1	0.92	1.87	2.779 (4)	167
O1W—H1B···O3iii	0.85	2.04	2.884 (4)	172
O2W—H2A···O2	0.84	1.80	2.633 (5)	170
N2—H2N···O1	0.86	1.87	2.724 (5)	174
N4—H4N···O4iv	0.86	1.90	2.759 (5)	177
N6—H6N···O4i	0.86	1.98	2.834 (5)	177
N8—H8N···O3v	0.86	2.04	2.876 (5)	165
N10—H10A···O2vi	0.86	1.87	2.638 (8)	149

Table 1

Selected bond lengths (Å)

Ni1—N1	2.104 (3)
Ni1—N3	2.120 (4)
Ni1—N5	2.128 (4)
Ni2—O1W	2.140 (3)
Ni2—O2W	2.025 (4)
Ni2—N7	2.108 (4)
Ni2—N9	2.048 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O1	0.92	1.87	2.779 (4)	167
O1W—H1B⋯O3i	0.85	2.04	2.884 (4)	172
O2W—H2A⋯O2	0.84	1.80	2.633 (5)	170
N2—H2N⋯O1	0.86	1.87	2.724 (5)	174
N4—H4N⋯O4ii	0.86	1.90	2.759 (5)	177
N6—H6N⋯O4iii	0.86	1.98	2.834 (5)	177
N8—H8N⋯O3iv	0.86	2.04	2.876 (5)	165
N10—H10A⋯O2v	0.86	1.87	2.638 (8)	149

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