A novel one-dimensional copper(II) coordination polymer and a trinuclear nickel(II) complex with a one-dimensional hydrogen-bonded structure

In the Cu^II compound catena-poly[[copper(II)-μ-[2-({2-[2-(naphthalen-2-yl­oxy)-1-oxido­ethyl­idene]hydrazin-1-ylidene}­methyl)phenolato]] di­methyl­formamide monosolvate monohydrate], {[Cu(C₁₉H₁₄N₂O₃)]·C₃H₇NO·H₂O}_n, (I), the Cu^II cation is O,N,O′-chelated by one ligand and further N,O-chelated by a second ligand, and exhibits a distorted square-pyramidal coordination environment. The ligand acts as an overall penta­dentate bridge between two metal ions, thus forming a novel coordination polymer. In the trinuclear Ni^II compound di­aqua­bis­(1H-imidazole)­bis­[μ-2-oxido-N′-(1-oxido-2-phen­oxy­ethylidene)­benzo­hydrazidato]trinickel(II) di­methyl­form­amide tetra­solvate, [Ni₃(C₁₅H₁₁N₂O₄)₂(C₃H₄N₂)₂(H₂O)₂]·4C₃H₇NO, (II), the three Ni^II cations are directly linked by two trans diazine (N—N) bridges and are strictly collinear by symmetry. The central Ni^II cation, located on an inversion centre, is coordinated by two water O atoms and is further N,O-chelated by two 2-oxido-N′-(1-oxido-2-phen­oxy­ethylidene)­benzo­hydrazidate(3−) ligands in an elongated octa­hedral coordination geometry. The two terminal centrosymmetrically related Ni^II cations are coordinated by an imidazole ligand and O,N,O′-chelated by a hydrazidate ligand in a distorted square-planar coordination geometry. Hydrogen bonds link individual mol­ecules of (II) into a chain along [100].

Computing details

For both compounds, data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97/2 (Sheldrick, 2008).

(I) catena-Poly[[copper(II)-µ-[2-({2-[2-(naphthalen-2-yloxy)-1-oxidoethylidene]hydrazin-1-ylidene}methyl)phenolato]] dimethylformamide monosolvate monohydrate]

Crystal data

[Cu(C19H14N2O3)]·C3H7NO·H2O	F(000) = 980
Mr = 472.97	Dx = 1.454 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3261 reflections
a = 10.874 (4) Å	θ = 3.1–27.5°
b = 22.702 (8) Å	µ = 1.05 mm^−1
c = 9.137 (3) Å	T = 293 K
β = 106.701 (8)°	Prism, green
V = 2160.4 (13) Å^3	0.38 × 0.24 × 0.16 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID imaging-plate diffractometer	4922 independent reflections
Radiation source: fine-focus sealed tube	3261 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	h = −12→14
Tmin = 0.746, Tmax = 0.845	k = −29→29
20932 measured reflections	l = −11→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0449P)^2] where P = (Fo^2 + 2Fc^2)/3
4922 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 0.45 e Å^−3
2 restraints	Δρmin = −0.41 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.22469 (3)	0.276839 (14)	0.76683 (3)	0.04085 (12)
O1	0.09165 (19)	0.32967 (9)	0.77090 (17)	0.0529 (5)
O2	0.35735 (19)	0.22366 (8)	0.74037 (17)	0.0510 (5)
O3	0.3858 (2)	0.15040 (9)	0.41410 (18)	0.0568 (5)
N1	0.1897 (2)	0.28199 (9)	0.5478 (2)	0.0390 (5)
N2	0.2614 (2)	0.24276 (9)	0.48768 (19)	0.0392 (5)
C1	0.0278 (3)	0.36435 (13)	0.6588 (3)	0.0492 (7)
C2	0.0334 (3)	0.35888 (12)	0.5050 (3)	0.0486 (7)
C3	−0.0398 (3)	0.39776 (15)	0.3933 (3)	0.0702 (10)
H3A	−0.0370	0.3941	0.2929	0.084*
C4	−0.1145 (4)	0.44055 (18)	0.4283 (4)	0.0882 (13)
H4A	−0.1621	0.4659	0.3532	0.106*
C5	−0.1182 (4)	0.44561 (17)	0.5791 (4)	0.0865 (12)
H5A	−0.1682	0.4749	0.6047	0.104*
C6	−0.0496 (3)	0.40836 (15)	0.6895 (3)	0.0689 (10)
H6A	−0.0548	0.4126	0.7888	0.083*
C7	0.1100 (3)	0.31659 (12)	0.4573 (3)	0.0451 (7)
H7A	0.1018	0.3138	0.3534	0.054*
C8	0.3453 (3)	0.21523 (11)	0.5988 (2)	0.0419 (6)
C9	0.4375 (3)	0.17330 (13)	0.5631 (3)	0.0509 (7)
H9A	0.5178	0.1933	0.5701	0.061*
H9B	0.4549	0.1413	0.6367	0.061*
C10	0.4468 (3)	0.10244 (13)	0.3743 (3)	0.0497 (7)
C11	0.5663 (3)	0.08353 (13)	0.4510 (3)	0.0553 (8)
H11A	0.6121	0.1029	0.5396	0.066*
C12	0.6220 (3)	0.03484 (13)	0.3982 (3)	0.0557 (8)
C13	0.7478 (4)	0.01502 (17)	0.4716 (4)	0.0773 (11)
H13A	0.7966	0.0344	0.5587	0.093*
C14	0.7983 (4)	−0.03162 (19)	0.4173 (5)	0.0876 (12)
H14A	0.8812	−0.0440	0.4676	0.105*
C15	0.7280 (4)	−0.06119 (17)	0.2874 (5)	0.0834 (11)
H15A	0.7640	−0.0932	0.2511	0.100*
C16	0.6073 (4)	−0.04367 (15)	0.2131 (4)	0.0720 (9)
H16A	0.5608	−0.0640	0.1266	0.086*
C17	0.5506 (3)	0.00532 (13)	0.2654 (3)	0.0571 (8)
C18	0.4268 (3)	0.02601 (15)	0.1906 (4)	0.0661 (9)
H18A	0.3787	0.0067	0.1031	0.079*
C19	0.3755 (3)	0.07322 (14)	0.2419 (3)	0.0601 (8)
H19A	0.2935	0.0862	0.1897	0.072*
O4	−0.1633 (3)	0.23117 (16)	0.5544 (4)	0.1252 (13)
N3	−0.2914 (3)	0.29975 (15)	0.6060 (3)	0.0806 (9)
C20	−0.1981 (4)	0.2612 (2)	0.6446 (5)	0.0867 (12)
H20A	−0.1557	0.2566	0.7480	0.104*
C21	−0.3523 (5)	0.3130 (3)	0.4469 (5)	0.140 (2)
H21A	−0.3191	0.2873	0.3839	0.209*
H21B	−0.3349	0.3532	0.4267	0.209*
H21C	−0.4433	0.3074	0.4245	0.209*
C22	−0.3309 (5)	0.3340 (2)	0.7182 (6)	0.1239 (18)
H22A	−0.2875	0.3198	0.8187	0.186*
H22B	−0.4220	0.3302	0.7002	0.186*
H22C	−0.3095	0.3746	0.7100	0.186*
O1W	0.0435 (3)	0.16060 (13)	0.5727 (3)	0.0790 (7)
H1W	−0.026 (2)	0.1801 (15)	0.555 (4)	0.083 (13)*
H2W	0.052 (3)	0.1599 (16)	0.488 (2)	0.077 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0545 (2)	0.0497 (2)	0.02148 (15)	0.00126 (16)	0.01581 (13)	−0.00012 (12)
O1	0.0627 (12)	0.0693 (13)	0.0306 (8)	0.0124 (10)	0.0195 (8)	−0.0002 (9)
O2	0.0647 (12)	0.0661 (12)	0.0226 (7)	0.0156 (10)	0.0130 (8)	0.0006 (8)
O3	0.0711 (13)	0.0633 (13)	0.0326 (8)	0.0201 (11)	0.0096 (9)	−0.0056 (8)
N1	0.0526 (13)	0.0421 (12)	0.0252 (9)	0.0011 (10)	0.0160 (9)	−0.0010 (8)
N2	0.0542 (13)	0.0441 (12)	0.0231 (9)	0.0060 (10)	0.0173 (10)	0.0022 (8)
C1	0.0558 (17)	0.0569 (17)	0.0360 (12)	0.0039 (14)	0.0148 (13)	−0.0043 (12)
C2	0.0581 (17)	0.0527 (17)	0.0359 (12)	0.0085 (14)	0.0150 (13)	0.0010 (12)
C3	0.091 (3)	0.075 (2)	0.0450 (15)	0.029 (2)	0.0210 (16)	0.0076 (15)
C4	0.112 (3)	0.093 (3)	0.0593 (19)	0.053 (3)	0.025 (2)	0.0144 (18)
C5	0.100 (3)	0.091 (3)	0.068 (2)	0.046 (2)	0.023 (2)	−0.004 (2)
C6	0.078 (2)	0.083 (2)	0.0483 (15)	0.0262 (19)	0.0229 (16)	−0.0055 (16)
C7	0.0586 (17)	0.0519 (16)	0.0263 (11)	0.0008 (14)	0.0144 (11)	0.0028 (11)
C8	0.0526 (16)	0.0497 (16)	0.0274 (11)	−0.0001 (13)	0.0177 (11)	−0.0017 (10)
C9	0.0625 (18)	0.0597 (18)	0.0311 (11)	0.0064 (15)	0.0142 (12)	−0.0034 (12)
C10	0.0613 (19)	0.0522 (17)	0.0390 (13)	0.0053 (14)	0.0196 (13)	−0.0001 (12)
C11	0.067 (2)	0.0593 (19)	0.0405 (13)	0.0061 (15)	0.0171 (14)	−0.0030 (13)
C12	0.071 (2)	0.0548 (18)	0.0486 (14)	0.0086 (16)	0.0286 (15)	0.0065 (13)
C13	0.080 (2)	0.086 (3)	0.0643 (19)	0.030 (2)	0.0176 (19)	0.0040 (18)
C14	0.090 (3)	0.090 (3)	0.088 (3)	0.035 (2)	0.032 (2)	0.015 (2)
C15	0.105 (3)	0.058 (2)	0.107 (3)	0.020 (2)	0.063 (3)	0.010 (2)
C16	0.095 (3)	0.053 (2)	0.081 (2)	−0.0040 (19)	0.047 (2)	−0.0072 (17)
C17	0.077 (2)	0.0449 (16)	0.0603 (16)	0.0017 (16)	0.0376 (17)	0.0002 (13)
C18	0.074 (2)	0.066 (2)	0.0602 (17)	−0.0120 (18)	0.0209 (17)	−0.0189 (16)
C19	0.0603 (19)	0.066 (2)	0.0525 (15)	0.0028 (16)	0.0146 (14)	−0.0125 (14)
O4	0.124 (3)	0.137 (3)	0.114 (2)	0.051 (2)	0.033 (2)	−0.029 (2)
N3	0.072 (2)	0.094 (2)	0.0735 (18)	0.0150 (18)	0.0172 (16)	−0.0088 (17)
C20	0.077 (3)	0.103 (3)	0.077 (2)	0.021 (2)	0.017 (2)	−0.006 (2)
C21	0.130 (4)	0.163 (5)	0.092 (3)	0.039 (4)	−0.021 (3)	−0.011 (3)
C22	0.138 (4)	0.126 (4)	0.127 (4)	0.038 (4)	0.069 (3)	−0.018 (3)
O1W	0.091 (2)	0.099 (2)	0.0561 (13)	0.0245 (16)	0.0344 (14)	0.0229 (14)

Geometric parameters (Å, º)

Cu1—O1	1.888 (2)	C11—C12	1.411 (4)
Cu1—N1	1.9304 (19)	C11—H11A	0.9300
Cu1—O2	1.949 (2)	C12—C17	1.408 (4)
Cu1—N2^i	1.9915 (18)	C12—C13	1.413 (5)
Cu1—O3^i	2.5008 (19)	C13—C14	1.351 (5)
O1—C1	1.320 (3)	C13—H13A	0.9300
O2—C8	1.277 (3)	C14—C15	1.387 (5)
O3—C10	1.377 (3)	C14—H14A	0.9300
O3—C9	1.414 (3)	C15—C16	1.352 (5)
N1—C7	1.280 (3)	C15—H15A	0.9300
N1—N2	1.396 (3)	C16—C17	1.419 (5)
N2—C8	1.312 (3)	C16—H16A	0.9300
N2—Cu1^ii	1.9915 (18)	C17—C18	1.404 (5)
C1—C6	1.386 (4)	C18—C19	1.353 (4)
C1—C2	1.430 (4)	C18—H18A	0.9300
C2—C3	1.410 (4)	C19—H19A	0.9300
C2—C7	1.419 (4)	O4—C20	1.212 (5)
C3—C4	1.362 (5)	N3—C20	1.309 (5)
C3—H3A	0.9300	N3—C21	1.445 (5)
C4—C5	1.395 (5)	N3—C22	1.446 (5)
C4—H4A	0.9300	C20—H20A	0.9300
C5—C6	1.363 (4)	C21—H21A	0.9600
C5—H5A	0.9300	C21—H21B	0.9600
C6—H6A	0.9300	C21—H21C	0.9600
C7—H7A	0.9300	C22—H22A	0.9600
C8—C9	1.485 (4)	C22—H22B	0.9600
C9—H9A	0.9700	C22—H22C	0.9600
C9—H9B	0.9700	O1W—H1W	0.850 (18)
C10—C11	1.356 (4)	O1W—H2W	0.808 (18)
C10—C19	1.402 (4)
O1—Cu1—N1	93.34 (8)	C11—C10—O3	125.2 (2)
O1—Cu1—O2	174.20 (6)	C11—C10—C19	120.4 (3)
N1—Cu1—O2	80.86 (8)	O3—C10—C19	114.4 (3)
O1—Cu1—N2^i	93.08 (8)	C10—C11—C12	120.9 (3)
N1—Cu1—N2^i	170.55 (9)	C10—C11—H11A	119.6
O2—Cu1—N2^i	92.70 (8)	C12—C11—H11A	119.6
O1—Cu1—O3^i	89.55 (8)	C17—C12—C11	118.9 (3)
O2—Cu1—O3^i	92.68 (8)	C17—C12—C13	118.4 (3)
N1—Cu1—O3^i	114.62 (8)	C11—C12—C13	122.7 (3)
N2^i—Cu1—O3^i	72.36 (8)	C14—C13—C12	121.0 (3)
C1—O1—Cu1	126.80 (17)	C14—C13—H13A	119.5
C8—O2—Cu1	110.76 (16)	C12—C13—H13A	119.5
C10—O3—C9	117.2 (2)	C13—C14—C15	120.8 (4)
C7—N1—N2	119.25 (19)	C13—C14—H14A	119.6
C7—N1—Cu1	126.97 (18)	C15—C14—H14A	119.6
N2—N1—Cu1	113.78 (14)	C16—C15—C14	120.2 (4)
C8—N2—N1	110.02 (18)	C16—C15—H15A	119.9
C8—N2—Cu1^ii	124.75 (17)	C14—C15—H15A	119.9
N1—N2—Cu1^ii	124.68 (14)	C15—C16—C17	121.0 (3)
O1—C1—C6	119.2 (2)	C15—C16—H16A	119.5
O1—C1—C2	123.3 (2)	C17—C16—H16A	119.5
C6—C1—C2	117.5 (2)	C18—C17—C12	118.3 (3)
C3—C2—C7	117.4 (2)	C18—C17—C16	123.1 (3)
C3—C2—C1	118.9 (3)	C12—C17—C16	118.5 (3)
C7—C2—C1	123.7 (2)	C19—C18—C17	122.0 (3)
C4—C3—C2	121.8 (3)	C19—C18—H18A	119.0
C4—C3—H3A	119.1	C17—C18—H18A	119.0
C2—C3—H3A	119.1	C18—C19—C10	119.6 (3)
C3—C4—C5	118.6 (3)	C18—C19—H19A	120.2
C3—C4—H4A	120.7	C10—C19—H19A	120.2
C5—C4—H4A	120.7	C20—N3—C21	120.4 (4)
C6—C5—C4	121.0 (3)	C20—N3—C22	122.2 (4)
C6—C5—H5A	119.5	C21—N3—C22	117.2 (4)
C4—C5—H5A	119.5	O4—C20—N3	124.2 (4)
C5—C6—C1	122.2 (3)	O4—C20—H20A	117.9
C5—C6—H6A	118.9	N3—C20—H20A	117.9
C1—C6—H6A	118.9	N3—C21—H21A	109.5
N1—C7—C2	124.4 (2)	N3—C21—H21B	109.5
N1—C7—H7A	117.8	H21A—C21—H21B	109.5
C2—C7—H7A	117.8	N3—C21—H21C	109.5
O2—C8—N2	124.0 (2)	H21A—C21—H21C	109.5
O2—C8—C9	116.0 (2)	H21B—C21—H21C	109.5
N2—C8—C9	119.9 (2)	N3—C22—H22A	109.5
O3—C9—C8	109.9 (2)	N3—C22—H22B	109.5
O3—C9—H9A	109.7	H22A—C22—H22B	109.5
C8—C9—H9A	109.7	N3—C22—H22C	109.5
O3—C9—H9B	109.7	H22A—C22—H22C	109.5
C8—C9—H9B	109.7	H22B—C22—H22C	109.5
H9A—C9—H9B	108.2	H1W—O1W—H2W	99 (3)
N1—Cu1—O1—C1	−13.2 (2)	Cu1—O2—C8—C9	−177.4 (2)
O2—Cu1—O1—C1	−11.2 (10)	N1—N2—C8—O2	0.3 (4)
N2^i—Cu1—O1—C1	173.8 (2)	Cu1^ii—N2—C8—O2	−171.5 (2)
O1—Cu1—O2—C8	−8.3 (10)	N1—N2—C8—C9	−176.9 (2)
N1—Cu1—O2—C8	−6.38 (18)	Cu1^ii—N2—C8—C9	11.3 (4)
N2^i—Cu1—O2—C8	166.65 (19)	C10—O3—C9—C8	−167.3 (2)
O1—Cu1—N1—C7	6.5 (2)	O2—C8—C9—O3	157.0 (2)
O2—Cu1—N1—C7	−173.3 (2)	N2—C8—C9—O3	−25.6 (4)
N2^i—Cu1—N1—C7	139.2 (5)	C9—O3—C10—C11	−15.4 (4)
O1—Cu1—N1—N2	−173.39 (17)	C9—O3—C10—C19	165.4 (3)
O2—Cu1—N1—N2	6.81 (17)	O3—C10—C11—C12	−178.1 (3)
N2^i—Cu1—N1—N2	−40.7 (6)	C19—C10—C11—C12	1.0 (5)
C7—N1—N2—C8	174.2 (2)	C10—C11—C12—C17	−1.1 (5)
Cu1—N1—N2—C8	−5.9 (3)	C10—C11—C12—C13	177.7 (3)
C7—N1—N2—Cu1^ii	−14.0 (3)	C17—C12—C13—C14	−0.8 (6)
Cu1—N1—N2—Cu1^ii	165.92 (11)	C11—C12—C13—C14	−179.6 (4)
Cu1—O1—C1—C6	−167.8 (2)	C12—C13—C14—C15	0.3 (6)
Cu1—O1—C1—C2	12.5 (4)	C13—C14—C15—C16	−0.1 (7)
O1—C1—C2—C3	179.3 (3)	C14—C15—C16—C17	0.5 (6)
C6—C1—C2—C3	−0.4 (4)	C11—C12—C17—C18	0.4 (5)
O1—C1—C2—C7	−1.4 (5)	C13—C12—C17—C18	−178.5 (3)
C6—C1—C2—C7	178.9 (3)	C11—C12—C17—C16	−179.9 (3)
C7—C2—C3—C4	−178.8 (4)	C13—C12—C17—C16	1.2 (5)
C1—C2—C3—C4	0.6 (5)	C15—C16—C17—C18	178.6 (3)
C2—C3—C4—C5	−0.1 (7)	C15—C16—C17—C12	−1.1 (5)
C3—C4—C5—C6	−0.5 (7)	C12—C17—C18—C19	0.4 (5)
C4—C5—C6—C1	0.7 (6)	C16—C17—C18—C19	−179.3 (3)
O1—C1—C6—C5	−179.9 (3)	C17—C18—C19—C10	−0.5 (5)
C2—C1—C6—C5	−0.2 (5)	C11—C10—C19—C18	−0.2 (5)
N2—N1—C7—C2	−179.0 (3)	O3—C10—C19—C18	178.9 (3)
Cu1—N1—C7—C2	1.1 (4)	C21—N3—C20—O4	−6.1 (8)
C3—C2—C7—N1	173.6 (3)	C22—N3—C20—O4	179.0 (5)
C1—C2—C7—N1	−5.8 (5)	Cu1—N1—N2—Cu1^ii	165.92 (11)
Cu1—O2—C8—N2	5.3 (3)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O4	0.85 (2)	1.89 (2)	2.726 (4)	168 (4)
O1W—H2W···O1^ii	0.81 (2)	2.16 (2)	2.959 (3)	171 (4)

Symmetry code: (ii) x, −y+1/2, z−1/2.

(II) Diaquabis(1H-imidazole)bis[µ-2-oxido-N'-(1-oxido-2-phenoxyethylidene)benzohydrazidato]trinickel(II) dimethylformamide tetrasolvate

Crystal data

[Ni3(C15H11N2O4)2(C3H4N2)2(H2O)2]·4C3H7NO	Z = 1
Mr = 1207.23	F(000) = 630
Triclinic, P1	Dx = 1.474 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.978 (5) Å	Cell parameters from 3982 reflections
b = 11.653 (5) Å	θ = 3.1–27.5°
c = 12.276 (8) Å	µ = 1.10 mm^−1
α = 80.87 (2)°	T = 293 K
β = 64.41 (2)°	Block, red
γ = 74.069 (16)°	0.37 × 0.24 × 0.10 mm
V = 1360.5 (13) Å^3

Data collection

Rigaku R-AXIS RAPID imaging-plate diffractometer	6158 independent reflections
Radiation source: fine-focus sealed tube	3982 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	h = −13→14
Tmin = 0.735, Tmax = 0.896	k = −13→15
13399 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0476P)^2] where P = (Fo^2 + 2Fc^2)/3
6158 reflections	(Δ/σ)max < 0.001
362 parameters	Δρmax = 0.39 e Å^−3
2 restraints	Δρmin = −0.43 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.10852 (3)	0.36024 (3)	0.74443 (3)	0.03282 (12)
Ni2	0.5000	0.5000	0.5000	0.03116 (14)
O1	0.15613 (19)	0.22377 (17)	0.82605 (19)	0.0415 (5)
O2	0.52233 (18)	0.33601 (16)	0.58391 (18)	0.0370 (5)
O3	0.06367 (18)	0.49903 (16)	0.65818 (18)	0.0388 (5)
O4	0.0477 (2)	0.74215 (17)	0.5630 (2)	0.0462 (6)
O5	0.5317 (2)	0.4245 (2)	0.3412 (2)	0.0424 (5)
N1	0.2857 (2)	0.37863 (18)	0.6615 (2)	0.0308 (5)
N2	0.2978 (2)	0.48165 (19)	0.5835 (2)	0.0322 (5)
N3	−0.0818 (2)	0.3510 (2)	0.8266 (2)	0.0387 (6)
N4	−0.3041 (3)	0.3797 (2)	0.8768 (3)	0.0526 (7)
H4B	−0.3846	0.4076	0.8755	0.063*
C1	0.2829 (3)	0.1683 (2)	0.8166 (3)	0.0332 (6)
C2	0.4054 (3)	0.2033 (2)	0.7367 (2)	0.0306 (6)
C3	0.5337 (3)	0.1366 (2)	0.7377 (3)	0.0404 (7)
H3A	0.6149	0.1601	0.6853	0.049*
C4	0.5412 (3)	0.0388 (3)	0.8138 (3)	0.0493 (9)
H4A	0.6265	−0.0044	0.8130	0.059*
C5	0.4198 (3)	0.0045 (3)	0.8925 (3)	0.0501 (9)
H5A	0.4241	−0.0619	0.9450	0.060*
C6	0.2937 (3)	0.0671 (3)	0.8940 (3)	0.0428 (8)
H6A	0.2138	0.0421	0.9471	0.051*
C7	0.4086 (3)	0.3095 (2)	0.6555 (2)	0.0310 (6)
C8	0.1745 (3)	0.5372 (2)	0.5889 (3)	0.0338 (7)
C9	0.1631 (3)	0.6452 (3)	0.5060 (3)	0.0419 (8)
H9A	0.2482	0.6728	0.4749	0.050*
H9B	0.1540	0.6223	0.4378	0.050*
C10	0.0570 (3)	0.8096 (3)	0.6401 (3)	0.0418 (8)
C11	−0.0517 (3)	0.9084 (3)	0.6809 (3)	0.0557 (10)
H11A	−0.1227	0.9253	0.6545	0.067*
C12	−0.0556 (4)	0.9817 (3)	0.7600 (4)	0.0682 (11)
H12A	−0.1292	1.0480	0.7869	0.082*
C13	0.0485 (4)	0.9578 (4)	0.7999 (4)	0.0689 (11)
H13A	0.0460	1.0070	0.8539	0.083*
C14	0.1571 (4)	0.8593 (3)	0.7579 (3)	0.0606 (10)
H14A	0.2279	0.8427	0.7846	0.073*
C15	0.1639 (3)	0.7851 (3)	0.6779 (3)	0.0487 (8)
H15A	0.2385	0.7199	0.6499	0.058*
C16	−0.1875 (3)	0.4122 (3)	0.8004 (3)	0.0425 (7)
H16A	−0.1812	0.4698	0.7376	0.051*
C17	−0.2741 (3)	0.2950 (3)	0.9566 (4)	0.0645 (11)
H17A	−0.3356	0.2565	1.0200	0.077*
C18	−0.1366 (3)	0.2781 (3)	0.9255 (3)	0.0589 (10)
H18A	−0.0867	0.2251	0.9650	0.071*
O6	0.5779 (2)	0.5577 (2)	0.1243 (2)	0.0542 (6)
N5	0.7505 (3)	0.6389 (2)	−0.0199 (2)	0.0457 (7)
C19	0.6996 (4)	0.5670 (3)	0.0738 (3)	0.0485 (8)
H19A	0.7611	0.5187	0.1048	0.063 (11)*
C20	0.6587 (4)	0.7181 (4)	−0.0693 (4)	0.0812 (13)
H20A	0.5845	0.7675	−0.0072	0.122*
H20B	0.6209	0.6720	−0.0999	0.122*
H20C	0.7094	0.7677	−0.1339	0.122*
C21	0.8948 (4)	0.6467 (3)	−0.0728 (3)	0.0690 (11)
H21A	0.9439	0.5905	−0.0311	0.103*
H21B	0.8995	0.7261	−0.0658	0.103*
H21C	0.9362	0.6287	−0.1567	0.103*
O7	0.3056 (3)	0.3641 (2)	0.3476 (3)	0.0723 (8)
N6	0.3083 (3)	0.1840 (3)	0.4486 (3)	0.0583 (8)
C22	0.2463 (4)	0.2906 (3)	0.4188 (4)	0.0618 (10)
H22A	0.1498	0.3115	0.4548	0.074*
C23	0.2280 (5)	0.1080 (4)	0.5404 (4)	0.0883 (14)
H23A	0.1310	0.1458	0.5672	0.132*
H23B	0.2538	0.0950	0.6075	0.132*
H23C	0.2457	0.0328	0.5073	0.132*
C24	0.4589 (4)	0.1474 (3)	0.4003 (4)	0.0773 (12)
H24A	0.4979	0.1923	0.3261	0.116*
H24B	0.4880	0.0637	0.3852	0.116*
H24C	0.4901	0.1619	0.4577	0.116*
H5B	0.463 (3)	0.401 (3)	0.349 (3)	0.068 (13)*
H5C	0.546 (3)	0.469 (2)	0.282 (2)	0.051 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.02582 (19)	0.0346 (2)	0.0349 (2)	−0.00864 (16)	−0.01102 (16)	0.00576 (15)
Ni2	0.0233 (2)	0.0335 (3)	0.0319 (3)	−0.0087 (2)	−0.0091 (2)	0.0085 (2)
O1	0.0275 (10)	0.0423 (11)	0.0487 (14)	−0.0116 (9)	−0.0139 (10)	0.0154 (9)
O2	0.0228 (9)	0.0377 (10)	0.0412 (12)	−0.0076 (9)	−0.0083 (9)	0.0108 (9)
O3	0.0262 (10)	0.0413 (11)	0.0428 (13)	−0.0065 (9)	−0.0130 (9)	0.0094 (9)
O4	0.0334 (11)	0.0400 (11)	0.0646 (16)	−0.0013 (10)	−0.0256 (11)	0.0032 (10)
O5	0.0409 (13)	0.0503 (13)	0.0376 (14)	−0.0197 (11)	−0.0162 (11)	0.0102 (10)
N1	0.0253 (11)	0.0315 (11)	0.0340 (14)	−0.0078 (10)	−0.0130 (10)	0.0080 (10)
N2	0.0257 (12)	0.0339 (12)	0.0344 (14)	−0.0091 (10)	−0.0117 (10)	0.0080 (10)
N3	0.0324 (13)	0.0395 (13)	0.0434 (16)	−0.0121 (11)	−0.0152 (12)	0.0065 (11)
N4	0.0294 (13)	0.0582 (17)	0.067 (2)	−0.0102 (13)	−0.0188 (14)	0.0029 (15)
C1	0.0314 (14)	0.0328 (14)	0.0352 (17)	−0.0067 (12)	−0.0152 (13)	0.0024 (12)
C2	0.0265 (13)	0.0307 (14)	0.0323 (16)	−0.0047 (12)	−0.0119 (12)	0.0012 (11)
C3	0.0303 (15)	0.0390 (16)	0.0466 (19)	−0.0060 (13)	−0.0143 (14)	0.0051 (14)
C4	0.0370 (17)	0.0438 (17)	0.060 (2)	−0.0001 (15)	−0.0236 (17)	0.0116 (16)
C5	0.053 (2)	0.0404 (17)	0.053 (2)	−0.0091 (16)	−0.0258 (17)	0.0186 (15)
C6	0.0394 (16)	0.0423 (16)	0.0425 (19)	−0.0159 (14)	−0.0136 (14)	0.0119 (14)
C7	0.0290 (14)	0.0333 (14)	0.0300 (16)	−0.0072 (12)	−0.0117 (12)	−0.0007 (12)
C8	0.0300 (15)	0.0378 (15)	0.0300 (16)	−0.0087 (13)	−0.0101 (13)	0.0036 (12)
C9	0.0350 (16)	0.0423 (17)	0.0430 (19)	−0.0075 (14)	−0.0154 (14)	0.0083 (14)
C10	0.0364 (16)	0.0408 (16)	0.047 (2)	−0.0148 (14)	−0.0174 (15)	0.0123 (14)
C11	0.0326 (17)	0.052 (2)	0.075 (3)	−0.0006 (16)	−0.0203 (17)	−0.0030 (18)
C12	0.054 (2)	0.061 (2)	0.075 (3)	−0.0054 (19)	−0.013 (2)	−0.019 (2)
C13	0.061 (2)	0.086 (3)	0.056 (3)	−0.030 (2)	−0.011 (2)	−0.012 (2)
C14	0.050 (2)	0.077 (3)	0.061 (3)	−0.031 (2)	−0.0234 (19)	0.010 (2)
C15	0.0366 (17)	0.0447 (18)	0.062 (2)	−0.0120 (15)	−0.0189 (16)	0.0065 (16)
C16	0.0329 (16)	0.0484 (18)	0.044 (2)	−0.0109 (14)	−0.0150 (14)	0.0030 (14)
C17	0.0385 (18)	0.059 (2)	0.086 (3)	−0.0238 (17)	−0.0197 (19)	0.029 (2)
C18	0.0419 (19)	0.054 (2)	0.070 (3)	−0.0146 (17)	−0.0210 (18)	0.0246 (18)
O6	0.0391 (12)	0.0726 (15)	0.0465 (14)	−0.0204 (12)	−0.0134 (11)	0.0101 (11)
N5	0.0456 (15)	0.0464 (14)	0.0380 (16)	−0.0106 (13)	−0.0113 (13)	0.0005 (12)
C19	0.050 (2)	0.0524 (19)	0.040 (2)	−0.0083 (17)	−0.0187 (17)	0.0018 (15)
C20	0.085 (3)	0.073 (3)	0.082 (3)	−0.017 (2)	−0.044 (3)	0.033 (2)
C21	0.053 (2)	0.073 (2)	0.059 (3)	−0.023 (2)	0.0033 (19)	−0.0058 (19)
O7	0.0782 (18)	0.0684 (16)	0.100 (2)	−0.0377 (15)	−0.0624 (17)	0.0309 (15)
N6	0.076 (2)	0.0545 (17)	0.057 (2)	−0.0305 (17)	−0.0332 (17)	0.0094 (14)
C22	0.061 (2)	0.071 (2)	0.074 (3)	−0.030 (2)	−0.042 (2)	0.008 (2)
C23	0.128 (4)	0.085 (3)	0.072 (3)	−0.066 (3)	−0.045 (3)	0.029 (2)
C24	0.073 (3)	0.060 (2)	0.098 (4)	−0.010 (2)	−0.037 (3)	−0.003 (2)

Geometric parameters (Å, º)

Ni1—O1	1.8156 (19)	C9—H9B	0.9700
Ni1—N1	1.821 (2)	C10—C11	1.383 (4)
Ni1—O3	1.8571 (19)	C10—C15	1.386 (4)
Ni1—N3	1.914 (3)	C11—C12	1.372 (5)
Ni2—O2^i	2.0271 (19)	C11—H11A	0.9300
Ni2—O2	2.0271 (19)	C12—C13	1.374 (5)
Ni2—N2^i	2.061 (2)	C12—H12A	0.9300
Ni2—N2	2.061 (2)	C13—C14	1.383 (5)
Ni2—O5^i	2.118 (3)	C13—H13A	0.9300
Ni2—O5	2.118 (3)	C14—C15	1.374 (5)
O1—C1	1.326 (3)	C14—H14A	0.9300
O2—C7	1.267 (3)	C15—H15A	0.9300
O3—C8	1.298 (3)	C16—H16A	0.9300
O4—C10	1.373 (4)	C17—C18	1.351 (4)
O4—C9	1.439 (3)	C17—H17A	0.9300
O5—H5B	0.832 (18)	C18—H18A	0.9300
O5—H5C	0.809 (17)	O6—C19	1.234 (4)
N1—C7	1.346 (3)	N5—C19	1.316 (4)
N1—N2	1.410 (3)	N5—C20	1.441 (4)
N2—C8	1.308 (3)	N5—C21	1.453 (4)
N3—C16	1.324 (3)	C19—H19A	0.9300
N3—C18	1.371 (4)	C20—H20A	0.9600
N4—C16	1.334 (4)	C20—H20B	0.9600
N4—C17	1.355 (4)	C20—H20C	0.9600
N4—H4B	0.8600	C21—H21A	0.9600
C1—C2	1.404 (4)	C21—H21B	0.9600
C1—C6	1.404 (4)	C21—H21C	0.9600
C2—C3	1.414 (4)	O7—C22	1.224 (4)
C2—C7	1.458 (4)	N6—C22	1.322 (4)
C3—C4	1.362 (4)	N6—C23	1.444 (4)
C3—H3A	0.9300	N6—C24	1.453 (5)
C4—C5	1.388 (4)	C22—H22A	0.9300
C4—H4A	0.9300	C23—H23A	0.9600
C5—C6	1.370 (4)	C23—H23B	0.9600
C5—H5A	0.9300	C23—H23C	0.9600
C6—H6A	0.9300	C24—H24A	0.9600
C8—C9	1.501 (4)	C24—H24B	0.9600
C9—H9A	0.9700	C24—H24C	0.9600
O1—Ni1—N1	94.50 (9)	O4—C9—H9B	108.8
O1—Ni1—O3	178.74 (9)	C8—C9—H9B	108.8
N1—Ni1—O3	84.39 (9)	H9A—C9—H9B	107.7
O1—Ni1—N3	89.38 (9)	O4—C10—C11	115.0 (3)
N1—Ni1—N3	176.11 (9)	O4—C10—C15	125.1 (3)
O3—Ni1—N3	91.74 (9)	C11—C10—C15	119.9 (3)
O2^i—Ni2—O2	180.000 (1)	C12—C11—C10	120.5 (3)
O2^i—Ni2—N2^i	78.33 (8)	C12—C11—H11A	119.7
O2—Ni2—N2^i	101.67 (8)	C10—C11—H11A	119.7
O2^i—Ni2—N2	101.67 (8)	C11—C12—C13	120.4 (4)
O2—Ni2—N2	78.33 (8)	C11—C12—H12A	119.8
N2^i—Ni2—N2	180.00 (12)	C13—C12—H12A	119.8
O2^i—Ni2—O5^i	91.17 (9)	C12—C13—C14	118.6 (4)
O2—Ni2—O5^i	88.83 (9)	C12—C13—H13A	120.7
N2^i—Ni2—O5^i	91.58 (9)	C14—C13—H13A	120.7
N2—Ni2—O5^i	88.42 (9)	C15—C14—C13	122.1 (4)
O2^i—Ni2—O5	88.83 (9)	C15—C14—H14A	119.0
O2—Ni2—O5	91.17 (9)	C13—C14—H14A	119.0
N2^i—Ni2—O5	88.42 (9)	C14—C15—C10	118.5 (3)
N2—Ni2—O5	91.58 (9)	C14—C15—H15A	120.7
O5^i—Ni2—O5	180.00 (6)	C10—C15—H15A	120.7
C1—O1—Ni1	126.76 (18)	N3—C16—N4	110.5 (3)
C7—O2—Ni2	114.01 (16)	N3—C16—H16A	124.8
C8—O3—Ni1	110.19 (16)	N4—C16—H16A	124.8
C10—O4—C9	118.7 (2)	C18—C17—N4	106.0 (3)
Ni2—O5—H5B	112 (3)	C18—C17—H17A	127.0
Ni2—O5—H5C	115 (2)	N4—C17—H17A	127.0
H5B—O5—H5C	105 (3)	C17—C18—N3	109.5 (3)
C7—N1—N2	113.5 (2)	C17—C18—H18A	125.2
C7—N1—Ni1	132.28 (19)	N3—C18—H18A	125.2
N2—N1—Ni1	114.14 (15)	C19—N5—C20	119.1 (3)
C8—N2—N1	108.6 (2)	C19—N5—C21	122.9 (3)
C8—N2—Ni2	139.81 (19)	C20—N5—C21	117.8 (3)
N1—N2—Ni2	111.55 (15)	O6—C19—N5	126.2 (3)
C16—N3—C18	105.7 (3)	O6—C19—H19A	116.9
C16—N3—Ni1	127.8 (2)	N5—C19—H19A	116.9
C18—N3—Ni1	126.6 (2)	N5—C20—H20A	109.5
C16—N4—C17	108.3 (2)	N5—C20—H20B	109.5
C16—N4—H4B	125.8	H20A—C20—H20B	109.5
C17—N4—H4B	125.8	N5—C20—H20C	109.5
O1—C1—C2	125.3 (2)	H20A—C20—H20C	109.5
O1—C1—C6	116.6 (3)	H20B—C20—H20C	109.5
C2—C1—C6	118.1 (2)	N5—C21—H21A	109.5
C1—C2—C3	119.2 (2)	N5—C21—H21B	109.5
C1—C2—C7	123.8 (2)	H21A—C21—H21B	109.5
C3—C2—C7	117.0 (2)	N5—C21—H21C	109.5
C4—C3—C2	121.5 (3)	H21A—C21—H21C	109.5
C4—C3—H3A	119.2	H21B—C21—H21C	109.5
C2—C3—H3A	119.2	C22—N6—C23	120.4 (4)
C3—C4—C5	119.0 (3)	C22—N6—C24	120.5 (3)
C3—C4—H4A	120.5	C23—N6—C24	118.7 (3)
C5—C4—H4A	120.5	O7—C22—N6	125.3 (4)
C6—C5—C4	121.0 (3)	O7—C22—H22A	117.4
C6—C5—H5A	119.5	N6—C22—H22A	117.4
C4—C5—H5A	119.5	N6—C23—H23A	109.5
C5—C6—C1	121.1 (3)	N6—C23—H23B	109.5
C5—C6—H6A	119.4	H23A—C23—H23B	109.5
C1—C6—H6A	119.4	N6—C23—H23C	109.5
O2—C7—N1	121.7 (2)	H23A—C23—H23C	109.5
O2—C7—C2	121.2 (2)	H23B—C23—H23C	109.5
N1—C7—C2	117.1 (2)	N6—C24—H24A	109.5
O3—C8—N2	122.6 (2)	N6—C24—H24B	109.5
O3—C8—C9	119.1 (2)	H24A—C24—H24B	109.5
N2—C8—C9	118.2 (2)	N6—C24—H24C	109.5
O4—C9—C8	113.7 (2)	H24A—C24—H24C	109.5
O4—C9—H9A	108.8	H24B—C24—H24C	109.5
C8—C9—H9A	108.8
N1—Ni1—O1—C1	−0.3 (2)	C2—C3—C4—C5	−0.4 (5)
O3—Ni1—O1—C1	28 (4)	C3—C4—C5—C6	0.4 (5)
N3—Ni1—O1—C1	180.0 (2)	C4—C5—C6—C1	−0.4 (5)
O2^i—Ni2—O2—C7	−111 (100)	O1—C1—C6—C5	−179.1 (3)
N2^i—Ni2—O2—C7	171.37 (19)	C2—C1—C6—C5	0.5 (5)
N2—Ni2—O2—C7	−8.63 (19)	Ni2—O2—C7—N1	8.3 (3)
O5^i—Ni2—O2—C7	80.0 (2)	Ni2—O2—C7—C2	−170.6 (2)
O5—Ni2—O2—C7	−100.0 (2)	N2—N1—C7—O2	−1.3 (4)
O1—Ni1—O3—C8	−29 (4)	Ni1—N1—C7—O2	174.7 (2)
N1—Ni1—O3—C8	−1.22 (19)	N2—N1—C7—C2	177.7 (2)
N3—Ni1—O3—C8	178.5 (2)	Ni1—N1—C7—C2	−6.3 (4)
O1—Ni1—N1—C7	5.1 (3)	C1—C2—C7—O2	−178.9 (3)
O3—Ni1—N1—C7	−174.3 (3)	C3—C2—C7—O2	4.3 (4)
N3—Ni1—N1—C7	−179 (67)	C1—C2—C7—N1	2.1 (4)
O1—Ni1—N1—N2	−178.89 (18)	C3—C2—C7—N1	−174.7 (3)
O3—Ni1—N1—N2	1.71 (18)	Ni1—O3—C8—N2	0.5 (4)
N3—Ni1—N1—N2	−2.7 (17)	Ni1—O3—C8—C9	176.8 (2)
C7—N1—N2—C8	175.0 (2)	N1—N2—C8—O3	0.8 (4)
Ni1—N1—N2—C8	−1.8 (3)	Ni2—N2—C8—O3	−177.6 (2)
C7—N1—N2—Ni2	−6.2 (3)	N1—N2—C8—C9	−175.5 (2)
Ni1—N1—N2—Ni2	177.09 (11)	Ni2—N2—C8—C9	6.1 (5)
O2^i—Ni2—N2—C8	6.1 (3)	C10—O4—C9—C8	75.6 (3)
O2—Ni2—N2—C8	−173.9 (3)	O3—C8—C9—O4	45.5 (4)
N2^i—Ni2—N2—C8	−170 (100)	N2—C8—C9—O4	−138.0 (3)
O5^i—Ni2—N2—C8	97.0 (3)	C9—O4—C10—C11	173.5 (3)
O5—Ni2—N2—C8	−83.0 (3)	C9—O4—C10—C15	−6.8 (4)
O2^i—Ni2—N2—N1	−172.25 (17)	O4—C10—C11—C12	178.9 (3)
O2—Ni2—N2—N1	7.75 (17)	C15—C10—C11—C12	−0.9 (5)
N2^i—Ni2—N2—N1	12 (100)	C10—C11—C12—C13	0.0 (6)
O5^i—Ni2—N2—N1	−81.38 (18)	C11—C12—C13—C14	0.5 (6)
O5—Ni2—N2—N1	98.62 (18)	C12—C13—C14—C15	0.0 (6)
O1—Ni1—N3—C16	−166.9 (3)	C13—C14—C15—C10	−0.9 (5)
N1—Ni1—N3—C16	16.9 (18)	O4—C10—C15—C14	−178.4 (3)
O3—Ni1—N3—C16	12.5 (3)	C11—C10—C15—C14	1.3 (5)
O1—Ni1—N3—C18	12.7 (3)	C18—N3—C16—N4	−0.9 (4)
N1—Ni1—N3—C18	−163.4 (15)	Ni1—N3—C16—N4	178.8 (2)
O3—Ni1—N3—C18	−167.8 (3)	C17—N4—C16—N3	0.7 (4)
Ni1—O1—C1—C2	−2.8 (4)	C16—N4—C17—C18	−0.1 (4)
Ni1—O1—C1—C6	176.6 (2)	N4—C17—C18—N3	−0.4 (5)
O1—C1—C2—C3	179.0 (3)	C16—N3—C18—C17	0.8 (4)
C6—C1—C2—C3	−0.5 (4)	Ni1—N3—C18—C17	−178.9 (3)
O1—C1—C2—C7	2.3 (5)	C20—N5—C19—O6	1.8 (5)
C6—C1—C2—C7	−177.2 (3)	C21—N5—C19—O6	178.6 (3)
C1—C2—C3—C4	0.5 (5)	C23—N6—C22—O7	175.5 (4)
C7—C2—C3—C4	177.4 (3)	C24—N6—C22—O7	2.9 (6)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O7	0.83 (2)	1.90 (2)	2.727 (4)	171 (4)
O5—H5C···O6	0.81 (2)	1.98 (2)	2.777 (3)	171 (3)
N4—H4B···O6^ii	0.86	2.05	2.897 (4)	170
C16—H16A···O7^ii	0.93	2.42	3.232 (4)	146
C22—H22A···O4^ii	0.93	2.52	3.262 (4)	137
C9—H9A···O2^i	0.97	2.28	3.200 (4)	159

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1.